Sodium hydride → 1-[2-(1-benzyl-pyrrolidin-3-yl)-ethyl]-5-fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

5-Fluoro-indole (391 mg, 2.89 mmol) in DMF (2 mL) was added drop-wise to a stirred suspension of sodium hydride (60%, 116 mg, 3.04 mmole) in DMF (2 mL) at 0° C. After 30 minutes compound a) (987 mg, 3.47 mmol), dissolved in DMF (6 mL), was added and the reaction mixture was stirred at 50° C. over night. The mixture was diluted with ethyl acetate, washed three times with water and dried over sodium sulfate. Evaporation of the solvent gave the crude product as a mixture of two constitution isomers. Silica gel chromatography (heptane-ethyl acetate-methanol, 20:80:5) gave the sub-title compound (138 mg, 15%) and 1-[2-(1-benzyl-pyrrolidin-3-yl)-ethyl]-5-fluoro-1H-indole (338 mg 36%).

Provenance & Evidence