1-(3-bromophenyl)-1H-imidazole → 3-[3-(Imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

Participants

Reaction Steps

To a degassed solution of 3-tributylstannyl-7-trifluoromethyl-imidazo[1,2-a]pyrimidine (1.4 mmol) was added 1-(3-bromophenyl)-1H-imidazole (0.60 g, 2.7 mmol) (prepared by the method of A. Johnson et al., J. Med. Chem., 1969, 12(5), 1024-8) and tetrakis(triphenylphosphine)-palladium(0) (218 mg, 0.18 mmol) and the mixture heated at reflux for 18 h. The crude reaction was adsorbed onto silica and chromatographed on silica, eluting on a gradient of 1 to 5% methanol in dichloromethane, to give a yellow oil. Crystallisation from ethyl acetatelisohexane afforded 3-[3-(imidazol-1-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine (0.098 g) as a white solid: δH (400 MHz; DMSO) 7.15 (1H, s), 7.53 (1H, d, J 7.4), 7.73 (1H, dd, J 3.1 and 1.6), 7.74 (1H, d, J 0.8), 7.78-7.81 (1H, m), 7.89 (1H, t, J 1.4), 8.08 (1H, dd, J 1.6 and 1.2), 8.39 (2H, d, J 7.0), 9.44 (1H, d, J 6.7); m/z (ES+) 330 (M++H).

Provenance & Evidence