Structure of 94569-84-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 94569-84-3 |
Formula : | C7H4BrFO |
M.W : | 203.01 |
SMILES Code : | C1=C(C(=CC=C1F)Br)C=O |
MDL No. : | MFCD00142872 |
InChI Key : | CJUCIKJLMFVWIS-UHFFFAOYSA-N |
Pubchem ID : | 2773321 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; In tetrahydrofuran; at 50℃; for 4h;Inert atmosphere; | General procedure: A two-necked dry flask was charged with the ortho-bromobenzaldehyde (10 mmol), the ethynylbenzene (1.22 g, 12 mmol), and freshly distilled THF 20 mL. Then Et3N (2.8 mL, 20 mmol, 2.0 equiv), PdCl2(PPh3)2 (210 mg, 0.36 mmol, 0.03 equiv), and CuI (95.2 mg, 0.6 mmol, 0.05 equiv) were added. The mixture was heated at 50 C for 4 h. After the reaction was complete (monitored by TLC), the solvents were evaporated under reduced pressure. The crude product was purified by column chromatography (SiO2, ethyl acetate/petroleum ether = 100: 1) to afford the ortho-alkynylbenzaldehyde. | |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; at 55℃;Inert atmosphere; | General procedure: To a solution of 2-bromobenzaldehyde (1.85 g, 10.0 mmol) and ethynylbenzene (1.124g,11.0 mmol) in Et3N (20.0 mL) was added Pd(PPh3)2Cl2 (140 mg, 2.0% mol) and CuI (20 mg,1.0% mol). The mixture was stirred at 55 oC for overnight. It was then quenched with water andwashed with ethyl acetate. After removal of solvent, the crude residue was purified by flashchromatography on silica gel (petroleum ether/ethyl acetate = 100:1, v/v) to afford the desiredproduct 2-(phenylethynyl)benzaldehyde (2.02 g, 98% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide; at 70℃; for 10h;Inert atmosphere; Schlenk technique; | General procedure: To a schlenk tube (15 mL) containing a solution of <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a (0.4 mmol) in DMSO (2 mL) was added 2-bromobenzaldehyde 4 (0.44 mmol) under nitrogen atmosphere.Then, the reaction mixture was stirred at 70C for 10 h until <strong>[32566-01-1]2-(1H-indol-2-yl)aniline</strong> 3a was consumed completely. Next, Pd(PPh3)2Cl2(0.02 mmol), [(t-Bu)3PH]BF4 (0.06 mmol) and Et3N (1.2 mmol) wereadded into the above reaction system under CO (1 atm) atmo-sphere. After being stirred at 120C for 5 h, the resulting mixturewas quenched with NH4Cl and extracted with ethyl acetate. Thecombined organic layer was washed with H2O and brine, and thendried over anhydrous Na2SO4. The solvent was removed underreduced pressure and the residue was puried by column chro-matography on silica gel (petroleum ether/ethyl acetate 5:1) toafford the corresponding indolo[1,2-c]isoindolo[2,1-a]quinazolin-5(16aH)-one 2. |
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