18628-07-4|9H-3,9'-Bicarbazole| Ambeed

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Quality Control of [ 18628-07-4 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 18628-07-4 ]

CAS No. :	18628-07-4
Formula :	C₂₄H₁₆N₂
M.W :	332.40
SMILES Code :	C1(NC2=C3C=CC=C2)=C3C=C(N4C5=C(C6=C4C=CC=C6)C=CC=C5)C=C1
MDL No. :	MFCD27644690
InChI Key :	FHJJVSJWFYYPAC-UHFFFAOYSA-N
Pubchem ID :	13236022

Safety of [ 18628-07-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 18628-07-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	26
Num. arom. heavy atoms	26
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	110.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.72 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.04
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	6.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	6.42
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.02
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	5.58
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.64
Solubility	0.0000753 mg/ml ; 0.000000227 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.69
Solubility	0.0000679 mg/ml ; 0.000000204 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-9.18
Solubility	0.000000218 mg/ml ; 0.0000000007 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.74 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.07

Application In Synthesis of [ 18628-07-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 18628-07-4 ]

[ 18628-07-4 ] Synthesis Path-Downstream 1~35

1
[ 18628-07-4 ]
[ 108-24-7 ]
3-carbazolyl-9-acetylcarbazole [ No CAS ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

2
[ 859938-50-4 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

3
[ 56-23-5 ]
[ 86-74-8 ]
[ 31892-44-1 ]
[ 1914-12-1 ]
[ 18628-07-4 ]
[ 6515-02-2 ]
[ 83415-87-6 ]

References: [1]Canadian Journal of Chemistry,1982,vol. 60,p. 2442 - 2450.

Yield	Reaction Conditions	Operation in experiment
84%	With dibenzo-18-crown-6; potassium acetate; copper; In N,N-dimethyl-formamide; at 120℃; for 4h;	General procedure: 2-aminobenzamide (1.4g, 0.010mol) in dibromochloromethane (2.1g, 0.010mol) dibenzo-18-crown-6 (1.1g, 0.0030mol), copper (2) (1.2g, 0.020mol), potassium acetate (2.8 g, 0.020mol), into a DMF in 100ml was reacted with stirring for 4 hours at 120 C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 1-1 1.1g (62% yield). Intermediate 1-8 (2.1g, 0.010mol) put in bromobenzene (1.6g, 0.010mol), by synthesis by the same method used in preparation Example 1-1 to give <Intermediate 1-9> 2.3g (yield 77%).
74%	With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;Inert atmosphere;	General procedure: 9 g (29.92 mmol) of Intermediate 1b and 50 mL of trifluoroacetic acid were dissolved in 80 mL of dichloromethane under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 30 minutes. After completion of the reaction, the reaction solution was neutralized with anhydrous MgSO4, filtered, and concentrated. The concentrated solution was recrystallized from dichloromethane and methanol, thus obtaining 6.8 g of Intermediate 1c (yield: 68%).

6
[ 867248-91-7 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With water; sodium hydroxide; In tetrahydrofuran; methanol; at 80℃; for 24h;	To a solution of 9-tosyl-9H-3,9'- bicarbazole or IC-2 (8.6 g, 17.6 mmol) in THF (150 mL) and methanol (60 mL), was added sodium hydroxide aqueous solution (10 g in 60 mL water). The mixture was heated at 80 C for 24 hours on a hot plate with a silicone oil bath. The resulting mixture was mixed with ethyl acetate and rinsed with brine, then loaded on silica gel (Grade 135) and purified by flash chromatography using eluents of ethyl acetate/hexanes (0% to 10%). After removal of solvents, the product was then collected to yield a white solid (Compound OSC-6) (5.0 g, in 86% yield). Confirmed by 1 HNMR.
77.9%	With potassium hydroxide; In tetrahydrofuran; ethanol; for 6h;Reflux;	d) 10.6 g (160.3 mmol) KOH 85% are dissolved in 450 ml EtOH, then 39.0 g (80.1 mmol) 3-Carbazol-9-yl-9-(p-tolylsulfonyl)carbazole dissolved in 180 ml THF are added and the clear solution is heated to reflux for 6 hours. The reaction mixture is cooled to RT and then added drop by drop to 1 l H2O. The resulting suspension is filtered and the residue is washed four times with H2O (200 ml each) and then dried at 80 C./125 mbar overnight to yield 25.6 g (96.1% of theory) of an off white solid. The crude product is suspended in 150 ml MeOH and heated to reflux for 2 hours. The suspension is cooled to RT and then to 0 C., filtered, washed twice with cold MeOH (20 ml each) and dried at 60 C./125 mbar overnight to yield 23.4 g (87.9%) of an off white solid. This procedure is repeated twice to yield 20.76 g (77.9% of theory) 3-Carbazol-9-yl-9H-carbazole as a white solid. 1H-NMR (400 MHz, CDCl3): delta 8.35-8.20 (m, 3H), 8.16 (br s, 1H), 8.08 (d, J=7.6 Hz, 1H), 7.64-7.28 (m, 11H).
	With sodium hydroxide; In tetrahydrofuran; methanol; water;	Step 4. 3-(9-carbazolyl)-9-tosylcarbazole (10.0 g, 21 mmol), NaOH (8.0 g, 200 mmol), 80 mL of THF, 40 mL of MeOH and 40 mL of water were added to a 500 mL round flask. The reaction was heated to reflux for 12 hours. After cooling, the mixture was purified by a silica gel column. The yield of 3-(9-carbazolyl)carbazole was 8 g.

3 g	With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;	Intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 ml) and methanol (18 ml) were added to a 100 ml three-necked round bottom flask and stirred at room temperature for 4 hours. Silica gel filtration and concentration under reduced pressure. The solid phase was washed with water and then recrystallized from dichloroethane to obtain 3 g of the title compound
3 g	With sodium hydride; In tetrahydrofuran; methanol; at 20℃; for 4h;	12 g of Intermediate 5-2, 1.0 g of sodium hydride, 36 mL of tetrahydrofuran and 18 mL of methanol were added to a 100 mL three-neck round bottom flask, and the mixture was stirred at room temperature for 4 hours. After silica gel filtration, the filtrate was concentrated under reduced pressure. The solid was washed with water and recrystallized from dichloroethane to give 3 g of the title compound.
3 g	With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;	In a 100 mL three-necked round bottom flask, intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 mL) and methanol (18 mL) were added and stirred at room temperature for 4 hours. The silica gel filter is then concentrated under reduced pressure. The solid phase was washed with water and then recrystallized with dichloroloethane to give 3 g of the title compound.

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817.
[2]Patent: WO2015/195837,2015,A1 .Location in patent: Paragraph 0061; 0064.
[3]Patent: US2016/248026,2016,A1 .Location in patent: Page/Page column 65.
[4]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886.
[5]Patent: US2009/134784,2009,A1 .
[6]Chemical Communications,2013,vol. 49,p. 6788 - 6790.
[7]Patent: KR2017/126059,2017,A .Location in patent: Paragraph 0104; 0105; 0111; 0112.
[8]Patent: KR2018/131662,2018,A .Location in patent: Paragraph 0134-0136; 0141-0142.
[9]Patent: KR2019/106313,2019,A .Location in patent: Paragraph 0206-0207.

7
[ 867248-84-8 ]
[ 18628-07-4 ]
[ 867248-86-0 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886.

8
[ 18628-07-4 ]
[ 100-44-7 ]
9-benzyl-3-(9-carbazolyl)-9H-carbazole [ No CAS ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886.

9
[ 861312-65-4 ]
[ 18628-07-4 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886.
[2]Chemical Communications,2013,vol. 49,p. 6788 - 6790.
[3]Patent: US2016/248026,2016,A1 .
[4]Patent: KR2017/126059,2017,A .
[5]Patent: KR2018/131662,2018,A .
[6]Patent: KR2019/106313,2019,A .

10
[ 86-74-8 ]
KOH [ No CAS ]
[ 18628-07-4 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 6883 - 6886.

11
[ 52708-37-9 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

12
[ 16982-76-6 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

13
[ 859078-81-2 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

14
[ 859084-99-4 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

15
[ 86-74-8 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.
[2]Patent: US2011/309345,2011,A1 .
[3]Chemical Communications,2013,vol. 49,p. 6788 - 6790.
[4]Patent: CN103159745,2016,B .
[5]Patent: CN103694992,2016,B .
[6]Patent: CN110467606,2019,A .

16
[ 100-00-5 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

17
[ 88-73-3 ]
[ 18628-07-4 ]

References: [1]Journal of the Chemical Society,1933,p. 1523.

18
[ 861312-65-4 ]
[ 18628-07-4 ]
[ 1014608-12-8 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817.

19
[ 18628-07-4 ]
[ 15164-44-0 ]
[ 1014608-07-1 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 1809 - 1817.

20
[ 18628-07-4 ]
[ 15164-44-0 ]
[ 1009639-02-4 ]

References: [1]Chemical Communications,2008,vol. 8,p. 453 - 455.

21
[ 109-65-9 ]
[ 18628-07-4 ]
[ 1133140-45-0 ]

References: [1]European Journal of Organic Chemistry,2009,p. 53 - 60.

22
[ 63790-78-3 ]
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
[ 18628-07-4 ]
[ 1158807-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Step 3. The 300 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 6-chlorobenzofuro[2,3-b]pyridine (2.04 g, 10 mmol), 3-(9-carbazolyl)carbazole (3.32 g, 10 mmol), Pd(OAc)2 (450 mg, 20 mol %), P(t-Bu)3 (10 mL of 1M solution in toluene, 10 mmol), potassium tert-buthoxide (1.92 g, 20 mmol) and 150 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 36 hours. Then the reaction was cooled down to room temperature, washed with water, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 4:1, providing 3.01 g of 6-(9H-3,9'-bicarbazol-9-yl)benzofuro[2,3-b]pyridine as white solid, structure was confirmed by NMR and MS spectroscopy.

References: [1]Patent: US2009/134784,2009,A1 .

23
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
8-iodo-3,4-dihydrodibenzo[b,d]furan [ No CAS ]
[ 18628-07-4 ]
[ 1158806-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Compound 16 The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-iodo-3,4-dihydrodibenzo[b,d]furan (332 mg, 1 mmol), 3-(9-carbazolyl)carbazole (294 mg, 1 mmol), Pd(OAc)2 (23 mg, 10 mol %), P(t-Bu)3 (1 mL of 1M solution in toluene, 1 mmol), potassium tert-buthoxide (150 mg, 1.5 eq) and 100 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 410 mg of 9-(dibenzo[b,d]furan-2-yl)-9H-3,9'-bicarbazole as white solid. The structure was confirmed by NMR and MS spectroscopy.

References: [1]Patent: US2009/134784,2009,A1 .

24
[ 13716-12-6 ]
potassium tert-buthoxide [ No CAS ]
[ 1161409-92-2 ]
[ 18628-07-4 ]
[ 1158807-01-2 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; toluene;	Step 3. The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-chlorobenzofuro[3,2-b]pyridine (2.04 g, 10 mmol), 3-(9-carbazolyl)carbazole (3.32 g, 10 mmol), Pd(OAc)2 (450 mg, 20 mol %), P(t-Bu)3 (10 mL of 1M solution in toluene, 10 mmol), potassium tert-buthoxide (1.92 g, 1.5 eq) and 150 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 2.5 g of 8-(9H-3,9'-bicarbazol-9-yl)benzofuro[3,2-b]pyridine as white solid. The structure was confirmed by NMR and MS spectroscopy.

References: [1]Patent: US2009/134784,2009,A1 .

25
[ 177775-86-9 ]
[ 86-74-8 ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With copper oxide; KOH; In tetrahydrofuran; methanol; hexane; N,N-dimethyl acetamide; water; ethyl acetate; toluene;	Synthesis Example 4 Synthesis of Compound 2-1 A mixture of 4.0 g of 9-Acetyl-3-bromocarbazole prepared as described above and 2.8 g of carbazole were stirred together in 30 ml N,N'-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170 C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid (5.0 g) was then taken up for further deprotection using 1.2 g KOH with THF (6 ml), methanol (12 ml) and water (12 ml) at reflux temperature. The reaction mixture was then extracted using ethylacetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene:hexane (1:2) as eluent, yielded 3.8 g of 3-(9-carbazolyl)carbazole as a white powder.

References: [1]Patent: US2011/309345,2011,A1 .

26
9-benzyl-3-(9-carbazolyl)-9H-carbazole [ No CAS ]
[ 18628-07-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium tert-butylate; oxygen; In tetrahydrofuran; dimethyl sulfoxide; for 3h;	Into a 100 ml round bottom flask, 0.19 g of a compound C2 (0.46 mmol), 14.3 ml of DMSO, and 4.58ml of potassiumt-butoxide in THF (1 M) was added, and the mixture was stirred for 10 minutes, and then oxygen was passed for 3 hours.The mixture was poured into 200 ml of water, stirred overnight, andfiltered to give a crude product, which was purified by column chromatography to give 0.14 g of product C3 in methylene chloride: petroleum ether = 1:5 (volume ratio). 92%.
83.1%	With potassium tert-butylate; oxygen; In dimethyl sulfoxide; at 20℃; for 5h;	2) In a 250 mL three-necked flask, add 0.05 mol of intermediate F-10 and 0.5 mol of potassium tert-butoxide, add 100 mL of DMSO to dissolve it, and bubbling with oxygen at room temperature for 5 h. Observe the reaction by thin layer chromatography (TLC) until The reaction is complete. After naturally cooling to room temperature, the reaction mixture was poured into 200 mL of water and stirred for 12 h. After standing for 30 min, it was filtered. The obtained material was purified through a silica gel column to obtain intermediate II-10, with a purity of 99.65% and a yield of 83.1%.
79%	With potassium tert-butylate; oxygen; In tetrahydrofuran; dimethyl sulfoxide; for 1h;	In a 200 mL reactor, compound (10-2) (3.3 g, 7.81 mmol, 1.0 eq), potassium tert-butoxide (t-BuOK, 6.13 g, 54.6 mmol, 7.0 eq.), Dimethyl sulfoxide (DMSO, 6.1 g, 78.1 mmol, 10 eq.), Tetrahydrofuran (THF, 55 mL) was added. While this solution was stirred, oxygen bubbling was performed for 1 hour (about 10 L). To the resulting orange suspension was added city water (200 mL), neutralized with 5% aqueous ammonium chloride solution, and the organic layers extracted sequentially with toluene (100 mL) and ethyl acetate (100 mL) were combined. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give an orange brown powder (3.34 g). This was subjected to column purification (SiO2 = 80 g, hexane / chloroform = 1/1 ? 1/2) to obtain a colorless solid (2.45 g). This was dispersed and washed with ethanol and dried under high vacuum to obtain a colorless solid compound (10-3) (2.01 g, 6.23 mmol, 79%).

References: [1]Patent: CN108191739,2018,A .Location in patent: Paragraph 0067; 0068; 0069.
[2]Chemical Communications,2012,vol. 48,p. 3015 - 3017.
[3]Patent: CN110467606,2019,A .Location in patent: Paragraph 0337-0338; 0341-0343.
[4]Patent: JP2019/172633,2019,A .Location in patent: Paragraph 0087; 0091; 0092.

27
3-bromo-9-benzyl-9H-carbazole [ No CAS ]
[ 18628-07-4 ]

References: [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017.
[2]Patent: CN108191739,2018,A .
[3]Patent: JP2019/172633,2019,A .
[4]Patent: CN110467606,2019,A .

28
[ 18628-07-4 ]
[ 18737-40-1 ]
C₄₈H₃₄N₂Si [ No CAS ]

References: [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017.

29
[ 18628-07-4 ]
[ 18733-91-0 ]
9-(4-((4-bromophenyl)diphenylsilyl)phenyl)-9H-3,9'-bicarbazole [ No CAS ]

References: [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017.
[2]Chemistry - A European Journal,2014,vol. 20,p. 2149 - 2153.

30
[ 18628-07-4 ]
[ 18733-91-0 ]
C₅₃H₃₇N₃Si [ No CAS ]

References: [1]Chemical Communications,2012,vol. 48,p. 3015 - 3017.

31
[ 1401234-58-9 ]
[ 18628-07-4 ]
[ 1401234-51-2 ]

References: [1]Advanced Functional Materials,2012,vol. 22,p. 2830 - 2836.

32
[ 1414960-14-7 ]
[ 18628-07-4 ]
[ 96042-30-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 5,5-dimethyl-1,3-cyclohexadiene;	Example 7 Synthesis of Compound 29 A suspension of (3-bromophenyl)(3-(dibenzo[b,d]furan-4-yl)phenyl)diphenylsilane (2.5 g, 4.30 mmol), 9H-3,9'-bicarbazole (1.715 g, 5.16 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol), SPhos (0.071 g, 0.172 mmol), and sodium tert-butoxide (0.826 g, 8.60 mmol) in xylene (50 mL) was refluxed at 140 C. under nitrogen overnight. After cooling to room temperature, the reaction was quenched with water and extracted with toluene. The organic phase was isolated, washed with water, and dried over MgSO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (8:2, v/v) as eluent, precipitation from DCM to ethanol to yield Compound 29 (2.86 g, 80%) as a white solid.

References: [1]Patent: US2012/298966,2012,A1 .

33
[ 1414941-45-9 ]
[ 18628-07-4 ]
[ 1414941-52-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In m-xylene; at 20℃;Inert atmosphere; Reflux;	Example 3: Synthesis of Compound 25[0114] A suspension of (3-bromophenyl)(3-(dibenzo[^

References: [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 59.

34
[ 1414941-46-0 ]
[ 18628-07-4 ]
[ 1414941-53-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In m-xylene; at 140℃;Inert atmosphere; Reflux;	Compound 26[0117] A suspension of (3-bromophenyl)(3'-(dibenzo[^

References: [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 60.

35
[ 1414960-14-7 ]
[ 18628-07-4 ]
[ 1414941-56-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In xylene; at 140℃;Inert atmosphere; Reflux;	Example 7: Synthesis of Compound 29[0124] A suspension of (3-bromophenyl)(3-(dibenzo[^

References: [1]Patent: WO2012/162325,2012,A1 .Location in patent: Page/Page column 62.

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CAS No.: 18628-07-4

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CAS No.: 18628-07-4

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[ 18628-07-4 ] Synthesis Path-Downstream 1~35

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