Borane → HCID 18914264, compound

Participants

Reaction Steps

To a stirred solution of N-[2-[2-(3,4-dimethoxy-phenyl)-1H-indol-3-yl]ethyl]-2-(4-nitrophenyl)acetamide (90 mg in 3 mL dry tetrahydrofuran) was added 0.79 mL of a 1M solution of borane in tetrahydrofuran and the mixture heated slowly to reflux on an oil bath. After 2 hours the mixture was cooled to room temperature and the excess borane quenched by the careful addition of methanol. The mixture was concentrated to half-volume, treated with N,N-dimethylethanolamine (0.60 mL) and heated to reflux on an oil bath. After 3 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol, 96:4) gave the title compound (79 mg).

Provenance & Evidence