Sodium hydride → HCID 51042485, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (20 mg, 0.51 mmol, 60%) in dry N,N-dimethylformamide (5 ml) at 25° C. was slowly added a solution of cyclopentyl-methanol (30 mg, 0.30 mmol; CAS Reg. No. 3637-61-4) in dry N,N-dimethylformamide (5 ml) and the suspension was stirred for 0.5 h. A solution of 2-(2-chloro-pyridin-3-yl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole (90 mg, 0.25 mmol) in N,N-dimethylformamide (5 ml) was then added drop wise to the above solution and further stirred for 16 h at 25° C. The reaction mixture was quenched with saturated aqueous solution of ammonium chloride. The solvents were removed under reduced pressure. The crude material dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (20-30% ethyl acetate/n-hexane) to afford the title compound as a colorless solid (54%). MS (Turbo Spray): m/z=426.3 (M+H).

Provenance & Evidence