Acetic Acid → HCID 86628684, compound

Participants

Reaction Conditions

Reaction Steps

Method Z-1 Place N-[3-(4-Cyano-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (500 mg, 1.41 mmol), sodium hyposulfite hydrate (311 mg, 3.53 mmol) and Raney nickel (50% soln in water, 700 μL, 2.96 mmol) in a round bottom flask then add water (6 mL), glacial acetic acid (12 mL) and pyridine (12 mL). Warm to 50° C., and stir for 1.5 hours. Cool to ambient temperature; dilute with water (10 mL); and extract with ethyl acetate (10 mL×3). Combine organic layers, and wash with saturated sodium bicarbonate, water (×3) and brine. Dry over sodium sulfate, and concentrate in vacuo. Purify residue by flash chromatography on silica (2-50% ethyl acetate in hexanes) to give N-[3-(4-formyl-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide (413.1 mg, 82%). LRMS (API ES−)=355.0 (M−H).

Provenance & Evidence