Sodium hydride → [1-Cyclopropylmethyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone

Participants

Reaction Conditions

Reaction Steps

A suspension of 0.15 g (0.28 mmol) [5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-[4-(piperidine-1-sulfonyl)-piperazin-1-yl]-methanone (example 2) and 14 mg (0.32 mmol; 55% dispersion in mineral oil) sodium hydride in 2 mL N,N-dimethyl-formamide was stirred 20 min. at 70° C. 34 μL (48 mg, 0.35 mmol) cyclopropylmethyl bromide were added and the solution was stirred another 45 min. at 70° C. After cooling to room temperature, the mixture was poured into 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 three times with water, brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with dichloromethane:methanol (9:1 v/v) as eluant to give 0.15 g (91%) of the desired compound as colorless foam. MS (ISP): 585.3 (M+H)+.

Provenance & Evidence