Imidazole → HCID 86680631, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of imidazole (0.034 g, 0.332 mmol) in DMF (3 ml) was added potassium carbonate (0.11 g, 0.83 mmol) and 4-(6-(1-bromopropyl)pyridin-3-yl)benzonitrile (0.090 g) under nitrogen and the solution was heated to 70° C. for 3 h. After cooling the contents to rt, sodium bicarbonate was added, extracted with ethyl acetate (50 mL), the organic layer separated, the organic layer dried over sodium sulphate and distilled off to obtain the crude product. The compound was purified by preparative TLC using (2000μ; 5% MeOH/DCM) to provide 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)cyclohexa-1,3-dienecarbonitrile (0.012 g, 13.9% yield). 1H NMR (400 MHz DMSO-d6): δ 8.96 (d, 1H), 8.19 (dd, 1H), 7.96 (d, 5H); 7.47 (d, 1H), 7.39 (s, 1H), 7.01 (s, 1H), 5.45 (t, 1H), 2.26-2.23 (m, 2H), 0.84 (t, 3H): LC-MS m/z calcd for [M+H]+ 289.14. found 289.0.

Provenance & Evidence