Sodium hydride → HCID 68682734, compound

Participants

Reaction Conditions

Reaction Steps

The suspension of 0.15 g (0.36 mmol) (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32) and 17 mg (0.36 mmol; 55% dispersion in mineral oil) sodium hydride in 2 mL N,N-dimethylformamide was stirred for 30 min. at 70° C. Then, 42 μL (58 mg, 0.43 mmol) cyclopropylmethyl bromide were added and the solution was stirred another 45 min. at 70° C. After cooling to room temperature the reaction was poured on 10% aqueous ammonium chloride solution and the phases were separated. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed twice with water, followed by brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to give 0.16 g (97%) of the desired compound as a colorless foam.

Provenance & Evidence