Bromoacetonitrile → 4-[4-(3-Chloro-4-fluoro-phenyl)-1-cyanomethyl-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Combine 4-[4-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (2.55 mmol; 969 mg), tetra-N-butylammonium bromide (0.26 mmol; 82 mg), 50 wt % aq sodium hydroxide (8.42 mmol; 0.45 mL) and DCM (25 mL). Add bromoacetonitrile (5.11 mmol; 0.36 mL) dropwise over 10 min. Stir 45 min and dilute with DCM, wash with brine, 50% saturated aqueous sodium chloride solution, dry over MgSO4, filter and evaporate. Purify over 150 g silica gel with 20% EA/DCM to provide the title compound (812 mg; 76%). MS (ES): m/z=419 (M+H).

Provenance & Evidence