Sodium hydride → 1-(3-chloro-1-phenyl-propyl)-1H-indazole-4-carbonitrile

Participants

Reaction Steps

Sodium hydride (0.092 g, 60% in oil) was added to a solution of 4-cyanoindazole (0.300 g) in N-methylpyrrolidinone (5 mL) and the reaction mixture was stirred at room temperature for 30 minutes. Methanesulfonic acid 3-chloro-1-phenyl-propyl ester (0.573 g) was added followed by 3 ml more of N-methylpyrrolidinone. The reaction mixture was stirred for an additional 6 hours at room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was washed with water, then with brine, and dried (MgSO4). Evaporation to dryness gave a residue which was purified by column chromatography on silica gel using ethyl acetate-hexane (1:9) to give 1-(3-chloro-1-phenyl-propyl)-1H-indazole-4-carbonitrile (0.228 g) as a foam, (M+H=297).

Provenance & Evidence