157869-15-3|2-((4-Methoxyphenyl)ethynyl)aniline| Ambeed

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Quality Control of [ 157869-15-3 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 157869-15-3 ]

CAS No. :	157869-15-3
Formula :	C₁₅H₁₃NO
M.W :	223.27
SMILES Code :	NC1=CC=CC=C1C#CC2=CC=C(OC)C=C2
MDL No. :	MFCD00168852
InChI Key :	YAXVIURCVHCTST-UHFFFAOYSA-N
Pubchem ID :	10878779

Safety of [ 157869-15-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 157869-15-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	12
Fraction Csp3	0.07
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	69.76
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.79
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	3.23
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.76
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.	3.13
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	3.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.72
Solubility	0.043 mg/ml ; 0.000193 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.64
Solubility	0.0508 mg/ml ; 0.000227 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.77
Solubility	0.00377 mg/ml ; 0.0000169 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
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	No
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	Yes
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.	-5.37 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	0.0
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	0.0
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	0.0
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	2.0 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)	2.1

Application In Synthesis of [ 157869-15-3 ]

* 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 [ 157869-15-3 ]

[ 157869-15-3 ] Synthesis Path-Downstream 1~35

1
[ 157869-15-3 ]
[ 157869-07-3 ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1733 - 1736.

2
[ 157869-15-3 ]
[ 5784-95-2 ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With zinc dibromide; In toluene; at 130℃; for 24h;	General procedure: To a stirred solution of the corresponding 2-iodoaniline (6, 1 mmol) in toluene (3 mL) under argon atmosphere were added Pd/CuO-Fe3O4 (50 mg), NaOH (400 mg, 10 mmol), and the corresponding alkyne (2, 1.5 mmol). The resulting mixture was stirred at 130 C until the end of reaction (see Table 6). The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was purified by chromatography on silica gel (hexane/ethyl acetate) to give the corresponding compounds 7. Yields are included in Table 6. Then, to a stirred solution of 7 (1 mmol) in toluene (4 mL) was added ZnBr2 (225 mg, 1 mmol). The resulting mixture was stirred at 130 C during 24 h. The mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to give the pure products 8 in quantitative yields. Physical and spectroscopic data for compounds 7 and 8, as well as literature for known compounds, follow.
91%	With silver nitrate; In water; at 130℃;Sealed tube; Sonication; Green chemistry;	General procedure: To a sealed tube (10 mL) was added 3-(phenylethynyl)pyridin-2-amine (1a; 50 mg, 0.26 mmol), H2O (2 mL), and AgNO3 (8.7 mg, 0.052 mmol). After ultrasonic oscillation for 5 min, the mixture was stirred at 130 C for about 16 h. The reaction product was filtered, washed with H2O, and dried to give a brown solid; yield: 48 mg (96%); mp 209-210 C; HPLC purity 98%.

References: [1]Tetrahedron,2012,vol. 68,p. 1393 - 1400.
[2]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3313 - 3318.
[3]Synthesis,2017,vol. 49,p. 4845 - 4852.
[4]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4983 - 4986.
[5]Angewandte Chemie - International Edition,2013,vol. 52,p. 11835 - 11839.
Angew. Chem.,2013,vol. 125,p. 12051 - 12055,5.
[6]Tetrahedron Letters,2009,vol. 50,p. 6877 - 6881.
[7]Tetrahedron,2010,vol. 66,p. 7169 - 7178.
[8]European Journal of Organic Chemistry,2007,p. 5332 - 5335.
[9]Journal of Organometallic Chemistry,1994,vol. 475,p. 289 - 296.
[10]Journal of Organometallic Chemistry,2010,vol. 695,p. 1675 - 1681.
[11]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 565 - 569.
[12]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3460 - 3465.
[13]Angewandte Chemie - International Edition,2019,vol. 58,p. 7687 - 7691.
Angew. Chem.,2019,vol. 131,p. 7769 - 7773,5.

3
[ 201230-82-2 ]
[ 157869-15-3 ]
[ 55164-80-2 ]
[ 170956-93-1 ]

References: [1]Tetrahedron Letters,1995,vol. 36,p. 6243 - 6246.

4
[ 157869-15-3 ]
[ 157869-07-3 ]
3-(4-Methoxy-phenyl)-cinnolin-4-ol [ No CAS ]

References: [1]Liebigs Annales,1995,p. 775 - 780.

5
[ 157869-15-3 ]
3-(4-Methoxy-phenyl)-cinnolin-4-ol [ No CAS ]

References: [1]Liebigs Annales,1995,p. 775 - 780.

6
[ 157869-15-3 ]
3-(4-Methoxy-phenyl)-cinnolin-4-ol [ No CAS ]
[ 7628-77-5 ]

References: [1]Liebigs Annales,1995,p. 775 - 780.

7
[ 615-43-0 ]
[ 768-60-5 ]
[ 157869-15-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: 2-iodoaniline (500.2 mg, 2.28 mmol, 1.0 equiv) was dissolved in Et3N (4.5 mL). The resulting solution was added with PdCl2(PPh3)2 (32.1 mg, 0.046 mol, 0.02 equiv) and CuI (17.4 mg, 0.091mmol, 0.04 equiv). The orange-yellow solution was degassed by bubbling with a stream of argon into the solution at room temperature for 30 min. After degassing, phenylacetylene (0.30 mL,279.0 mg, 2.73 mmol, 1.2 equiv) was added as a neat liquid into the solution via syringe. The resulting dark brown solution was allowed to stir at room temperature under argon atmosphere overnight. The reaction was quenched by addition of sat. aq. NH4Cl. The separated aqueousphase was extracted with EtOAc (3x times). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4, filtered and concentrated to a crude product. The crudeproduct was purified by SiO2 column chromatography eluting with 0-10% EtOAc-hexane to give 398.2 mg (90%) of 2-(phenylethynyl)aniline as an orange solid.
75%	With sodium hydroxide; In toluene; at 130℃; for 72h;	General procedure: To a stirred solution of the corresponding 2-iodoaniline (6, 1 mmol) in toluene (3 mL) under argon atmosphere were added Pd/CuO-Fe3O4 (50 mg), NaOH (400 mg, 10 mmol), and the corresponding alkyne (2, 1.5 mmol). The resulting mixture was stirred at 130 C until the end of reaction (see Table 6). The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was purified by chromatography on silica gel (hexane/ethyl acetate) to give the corresponding compounds 7. Yields are included in Table 6. Then, to a stirred solution of 7 (1 mmol) in toluene (4 mL) was added ZnBr2 (225 mg, 1 mmol). The resulting mixture was stirred at 130 C during 24 h. The mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to give the pure products 8 in quantitative yields. Physical and spectroscopic data for compounds 7 and 8, as well as literature for known compounds, follow.

References: [1]Dalton Transactions,2017,vol. 46,p. 1539 - 1545.
[2]Applied Organometallic Chemistry,2018,vol. 32.
[3]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 565 - 569.
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 11835 - 11839.
Angew. Chem.,2013,vol. 125,p. 12051 - 12055,5.
[5]New Journal of Chemistry,2018,vol. 42,p. 16886 - 16890.
[6]Tetrahedron Letters,2018,p. 675 - 680.
[7]Liebigs Annales,1995,p. 775 - 780.
[8]Applied Organometallic Chemistry,2014,vol. 28,p. 298 - 303.
[9]Journal of Organic Chemistry,2010,vol. 75,p. 3412 - 3419.
[10]Journal of Organic Chemistry,2019,vol. 84,p. 8121 - 8130.
[11]Tetrahedron,2012,vol. 68,p. 1393 - 1400.
[12]Synthesis,2009,p. 829 - 835.
[13]ChemMedChem,2016,vol. 11,p. 2347 - 2360.
[14]Tetrahedron Letters,2004,vol. 45,p. 35 - 38.
[15]Organic Letters,2008,vol. 10,p. 4887 - 4889.
[16]Journal of Organic Chemistry,2010,vol. 75,p. 7502 - 7504.
[17]Organic Letters,2011,vol. 13,p. 1098 - 1101.
[18]Journal of Organic Chemistry,2012,vol. 77,p. 617 - 625.
[19]Tetrahedron Letters,2013,vol. 54,p. 2357 - 2361.
[20]Chemistry - A European Journal,2013,vol. 19,p. 8294 - 8299.
[21]Journal of Organic Chemistry,2013,vol. 78,p. 10319 - 10328.
[22]Organic Letters,2013,vol. 15,p. 5940 - 5943.
[23]Chemical Communications,2014,vol. 50,p. 3024 - 3026.
[24]Chemistry - A European Journal,2015,vol. 21,p. 3193 - 3197.
[25]Organic Letters,2015,vol. 17,p. 5662 - 5665.
[26]Journal of Organic Chemistry,2016,vol. 81,p. 3994 - 4001.
[27]Chemical Communications,2017,vol. 53,p. 196 - 199.
[28]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1373 - 1378.
[29]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1844 - 1848.
[30]Chemical Communications,2017,vol. 53,p. 8533 - 8536.
[31]Chemical Communications,2017,vol. 53,p. 8980 - 8983.
[32]Organic Letters,2017,vol. 19,p. 3982 - 3985.
[33]Organic Letters,2017,vol. 19,p. 6128 - 6131.
[34]Journal of Organic Chemistry,2017,vol. 82,p. 12386 - 12394.
[35]Journal of Organic Chemistry,2018,vol. 83,p. 10453 - 10464.
[36]Organic Letters,2018,vol. 20,p. 6765 - 6768.
[37]Advanced Synthesis and Catalysis,2019,vol. 361,p. 490 - 495.
[38]Angewandte Chemie - International Edition,2019,vol. 58,p. 8882 - 8886.
Angew. Chem.,2019,vol. 131,p. 8974 - 8978,5.
[39]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5558 - 5564.
[40]Chemical Communications,2020,vol. 56,p. 474 - 477.
[41]Organic Letters,2020,vol. 22,p. 814 - 817.
[42]Journal of Organic Chemistry,2020,vol. 85,p. 3224 - 3233.

8
[ 157869-15-3 ]
(1H-indazol-3-yl)(4-methoxyphenyl)methanone [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 5453 - 5455.

9
[ 104-87-0 ]
[ 157869-15-3 ]
[2-(4-Methoxy-phenylethynyl)-phenyl]-[1-p-tolyl-meth-(E)-ylidene]-amine [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 35 - 38.

10
[ 201230-82-2 ]
[ 157869-15-3 ]
3-[1-chloro-1-(4-methoxylphenyl)methylidene]indolin-2-one [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 3413 - 3416.

11
[ 157869-15-3 ]
2-(4-methoxy-phenyl)-1-(methoxy-<i>p</i>-tolyl-methyl)-1<i>H</i>-indole [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 35 - 38.

12
[ 611-10-9 ]
[ 157869-15-3 ]
[ 1103523-13-2 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 1418 - 1421.

13
[ 16616-42-5 ]
[ 157869-15-3 ]
C₃₀H₂₂ClNO₂ [ No CAS ]

References: [1]Synlett,2009,p. 1245 - 1250.

14
[ 134419-77-5 ]
[ 157869-15-3 ]
C₃₀H₂₂BrNO₂ [ No CAS ]

References: [1]Synlett,2009,p. 1245 - 1250.

15
[ 103-71-9 ]
[ 157869-15-3 ]
[ 1096541-16-0 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4406 - 4412.

16
[ 1195-45-5 ]
[ 157869-15-3 ]
[ 1096541-31-9 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4406 - 4412.

17
[ 5416-93-3 ]
[ 157869-15-3 ]
[ 1096541-42-2 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 4406 - 4412.

18
[ 52670-38-9 ]
[ 696-62-8 ]
[ 157869-15-3 ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 14441 - 14448.
[2]European Journal of Organic Chemistry,2010,p. 818 - 822.
[3]Organic Letters,2013,vol. 15,p. 3710 - 3713.
[4]Organic Letters,2014,vol. 16,p. 3720 - 3723.
[5]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4652 - 4656.

19
[ 141-97-9 ]
[ 157869-15-3 ]
[ 1220451-84-2 ]

References: [1]European Journal of Organic Chemistry,2010,p. 818 - 822.

20
[ 590-28-3 ]
[ 157869-15-3 ]
[ 1201632-67-8 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6841 - 6843.

21
[ 768-60-5 ]
2-haloaniline [ No CAS ]
[ 157869-15-3 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6877 - 6881.

22
[ 157869-15-3 ]
[ 407-25-0 ]
[ 201813-47-0 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 3412 - 3419.

23
[ 137-26-8 ]
[ 157869-15-3 ]
(E)-4-(4-methoxybenzylidene)-N,N-dimethyl-4H-benzo[d][1,3]thiazin-2-amine [ No CAS ]
[ 1236003-89-6 ]

References: [1]Synlett,2010,p. 1345 - 1350.

24
[ 768-60-5 ]
2-aminophenyl halide [ No CAS ]
[ 157869-15-3 ]

References: [1]Tetrahedron,2010,vol. 66,p. 7169 - 7178.

25
[ 157869-15-3 ]
[ 2258-42-6 ]
[ 1200688-10-3 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7502 - 7504.

26
[ 157869-15-3 ]
[ 54888-64-1 ]

References: [1]Organic Letters,2009,vol. 11,p. 3598 - 3601.

27
[ 615-36-1 ]
[ 768-60-5 ]
[ 157869-15-3 ]

References: [1]Organic Letters,2009,vol. 11,p. 3598 - 3601.

28
[ 1142-19-4 ]
[ 157869-15-3 ]
[ 1285494-86-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 80℃;	A mixture of 2-alkynylaniline 1a-1e (0.2 mmol), dichalcogenide 2a-2e (0.15 mmol), CuI (0.02 mmol), and Cs2CO3 (0.2 mmol) in DMSO (2 mL) was stirred at 80 C under an air atmosphere. After completion of the reaction that was monitored by GC-MS or TLC, 25 mL water was added, and the mixture was extracted with ethyl acetate, the combined organic layers were washed with water (10 mL x 3), dried over anhydrous Na2SO4. After filtration and removal of solvents in vacuum, the residue was purified by silica gel column chromatography to afford the corresponding products.