2,6-Dibromopyridine → 3-(6-Bromopyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine

Participants

Reaction Steps

To the degassed solution of 3-tributylstannyl-7-trifluoromethyl-imidazo[1,2-α]pyrimidine was added 2,6-dibromopyridine (1.8 g, 7.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (218 mg, 0.18 mmol) and the mixture heated at reflux for 3 h. The crude reaction was adsorbed onto silica and purified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (20-60%) to give a yellow solid. Crystallisation from ethyl acetate/isohexane afforded 3-(6-bromopyridin-2-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (702 mg) as a white solid: δH (400 MHz, DMSO) 7.64 (1H, d, J 9), 7.83 (1H, d, J 8), 7.93 (1H, dd, J 9 and 9), 8.20 (1H, d, J 9), 8.92 (1H, s), 10.18 (1H, d, J 9); m/z (ES+) 343, 345 (M++H).

Provenance & Evidence