Dimethylformamide → 1-methyl-2-oxo-2,3-dihydro-1H-indole-6-carbonitrile

Participants

Reaction Steps

To a solution of 6-bromo-1-methyl-1,3-dihydro-indol-2-one (226 mg, 1.0 mmol) in DMF (6.0 mL) was added zinc cyanide (117 mg, 1.0 mmol). Then the reaction mixture was degassed and placed under an argon atmosphere and tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.1 mmol) was added. The reaction was then placed at 95° C. for 100 minutes, at which time it was cooled to room temperature, and diluted with saturated aqueous sodium bicarbonate and dichloromethane. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%) to furnish 1-methyl-2-oxo-2,3-dihydro-1H-indole-6-carbonitrile; MS: (ES+) m/z 173.0 (M+H)+.

Provenance & Evidence