Benzimidazole → 2-(1H-benzimidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide

Participants

Reaction Steps

A solution of potassium tert-butoxide (1.7 mL of 1 M solution in THF, 1.7 mmol,) was added to a solution of 1H-benzoimidazole (165 mg, 1.4 mmol) in anhydrous TBF (3 mL). The reaction mixture was stirred for 20 min at ambient temperature. 2-Bromo-N-(3-trifluoromethyl-phenyl)-acetamide (Example 92 part A) was added (261 mg, 0.93 mmol) and the mixture was stirred at 55° C. for subsequent 24 h. The crude product was purified on a preparative HPLC (XTerra C8 column 19×300 mm, 0.1 M aqueous NH4Ac/CH3CN). The pooled fractions were lyophilized to afford 81 mg (27%) of the title compound. Calculated for C16H12F3N3O m/z: 319.29, found 320.0 [M+H]+. 1H NMR (400 MeOH) δ ppm 5.2 (s, 2H), 7.3 (m, 2H), 7.4 (d, J=7.6 Hz, 1H), 7.5 (m, 2H), 7.7 (d,J=7.1 Hz, 1H), 7.8 (d, J=8.6 Hz, 1H), 8.0 (s, 1H), 8.2 (s, 1H).

Provenance & Evidence