Benzoyl chloride → HCID 21847948, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 2-(4-chlorophenyl)-1-methoxymethyl-5-(4-pyridyl)imidazole from Step B (40 mg, 0.13 mmol) in THF (0.5 mL) at -30° C. was added dropwise a solution of n-butyllithium in hexanes (93 μL of a 2.5 M solution, 0.23 mmol). The reaction was stirred at -30 to -10° C. for 90 min. After cooling to -30° C., benzoyl chloride (47 μL, 0.40 mmol) was added. The reaction was stirred overnight at room temperature. The reaction was quenched by the addition of saturated ammonium chloride solution and the mixture was extracted with ethyl acetate (2 times). The combined extracts were successively washed with water and saturated salt solution and dried over anhydrous sodium sulfate. The solution was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-4% methanol in methylene chloride to yield the title compound as a red-brown glass (14 mg, 26% yield), mass spectrum (CI) m/e=404 (M+1)+.

Provenance & Evidence