(+-)-2-Butanol → 1-(5-(4-chlorophenyl)-1-methyl-1H-imidazol-4-yl)-2-(3,5-difluorophenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(4-chlorophenyl)-1-methyl-1H-imidazole-4-carbonitrile (520 mg, 2.4 mmol) in toluene (13 mL) at 0° C. was added (3,5-difluorobenzyl)magnesium bromide (12.5 mL of a 0.25 M solution in diethylether). The reaction was stirred 20 min at 0° C. then let warm to ambient temperature. After stirring for 40 min, the reaction was cooled to 0° C. 2-Butanol (8 mL) and MeOH (4 mL) were added followed by addition of NaBH4 (135 mg, 3.6 mmol) and stirred for 20 min. The reaction was quenched by addition of saturated aqueous NH4Cl and extracted with EtOAc. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product. MS (m/z) 348.3 [M+H]+.

Provenance & Evidence