Methyl iodide → Methyl 5-(4-bromo-2-chloroanilino)-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylate

Participants

Reaction Steps

A solution of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester (150 mg, 0.38 mmol), iodomethane (28 μL, 0.45 mmol) and potassium carbonate (78 mg, 0.56 mmol) in dimethylformamide (1.5 mL) was stirred at 75° C. for one hour. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium carbonate (2×), brine and dried (Na2SO4). Flash column chromatography (20:1 methylene chloride/ethyl acetate) provided 56 mg (36%) of the more mobile 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester as a white solid. 19F NMR (376 MHz, CD3OD)—133.5 (s). MS APCI (+) m/z 412, 414 (M+, Br pattern) detected. Also isolated is 54 mg (35%) of 6-4(-bromo-2-chloro-phenylamino)-7-fluoro-1-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester as a white solid. 19F NMR (376 MHz, CD3OD)—139.9 (s). MS APCI (+) m/z 412, 414 (M+, Br pattern) detected.

Provenance & Evidence