Imidazole → HCID 71547904, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of imidazole (0.077 g, 1.12 mmol), in DMF (15 mL) was added potassium carbonate (0.26 g, 1.87 mmol) and 4-(6-(1-bromopropyl)pyridin-3-yl)benzamide under nitrogen and the solution was heated to 55-60° C. for 6 h. The contents were cooled to rt, diluted with water (100 mL), extracted with ethyl acetate (2×100 mL), the layers separated, the organic layer washed with brine solution (2×30 mL), the organic layer dried over sodium sulphate and distilled off to get the crude product. The product was purified by preparative TLC (2000; 5% methanol in ethyl acetate) to give 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzamide (15 mg, 13% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1H), 8.13 (d, 1H), 8.11 (s, 1H), 7.97 (d, 2H), 7.80 (t, 3H), 7.40 (d, 2H), 7.31 (s, 1H), 6.89 (s, 1H), 5.38 (q, 1H), 2.27 (m, 2H), 0.82 (t, 3H); LC-MS m/z calcd for [M+H]+ 307.37. found 307.3.

Provenance & Evidence