Acetyl chloride → HCID 24955342, compound

Participants

Reaction Steps

To a solution (5 mL) of (7-phenyl-1,2-dihydrofuro[2,3-e]imidazo[1,2-a]pyridin-8-yl)acetonitrile (17.0 mg, 0.062 mmol) in 2M ammonia/ethanol was added Raney cobalt (500 mg), and the mixture was stirred at room temperature for 2.5 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (2 mL), triethylamine (17.3 μL, 0.124 mmol) and acetyl chloride (5.3 μL, 0.074 mmol) were added, and the mixture was stirred at room temperature for 20 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/hexane) to give the title compound (12.9 mg, yield 65%).

Provenance & Evidence