Structure of 61995-52-6
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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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CAS No. : | 61995-52-6 |
Formula : | C10H8BrNO |
M.W : | 238.08 |
SMILES Code : | CC(=O)N1C=CC2=C1C=CC(Br)=C2 |
MDL No. : | MFCD00238530 |
InChI Key : | BOMKWHSZGCMFEG-UHFFFAOYSA-N |
Pubchem ID : | 12318076 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | 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 |
---|---|---|
66% | With dmap; triethylamine; In 1,2-dichloro-ethane; at 20 - 60℃; for 8h; | General procedure: Triethylamine (3.8 mmol, 1.5 equiv), acetic anhydride (9.6 mmol, 3.8 equiv) and DMAP(0.5 mmol, 0.2 equiv) were added at rt to a solution of 5-bromo-1H-indole (2.5 mmol, 1 equiv) in1,2 dichloroethane (10 mL). The solution was heated to 60 C for 8 h. When the reaction wascomplete [TLC (EtOAc/hexane 2:5)], the mixture was extracted with EtOAc (2 × 20 mL) andwashed with water (2 × 20 mL). The organic layer was separated, dried over anhydrous Na2SO4,filtered and the solvent removed under reduced pressure. The residue was purified by flashcolumn chromatography [silica gel (230-400 mesh; Merck), EtOAc/hexane 2:5]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 18h;Inert atmosphere; | General procedure: To a solution of N-alkyl bromoindole/indazoles (2, 2.4 mmol, 1 equiv) in DMF (5 mL) under anitrogen atmosphere was added CS2CO3 (7.2 mmol, 3 equiv), potassium vinyltrifluoroborate(4.8 mmol, 2 equiv) and PdCl2(dppf)CH2Cl2 adduct (0.24 mmol, 0.1 equiv). The reaction masswas heated to 90 C for 18 h. When the reaction was completed [TLC (EtOAc/hexane 2:5)], themixture was extracted with EtOAc (2 × 20 mL) and washed with water (2 × 20 mL). The organiclayer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Theresidue was purified by flash column chromatography [silica gel (230-400 mesh; Merck),EtOAc/hexane 2:5]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium carbonate; In acetonitrile; at 120℃; for 24h;Schlenk technique; | General procedure: A mixture of indole 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10 mmol, 20 mol%), and alkenyl carboxylate 2 (2.0 mmol, 4.0 equiv) in MeCN (3 mL) was added into a Schlenk flask (25 mL) and stirred at 120 C until completion of the reaction. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (petroleum ether/EtOAc 20:1 to 5:1) to afford the desired acylindoles 3 (Tables 2 and 3). |
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