5-Bromo-2-fluoropyridine → HCID 9835438, compound

Participants

Reaction Steps

To a degassed solution of 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine was added 5-bromo-2-fluoropyridine (0.128 ml, 1.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (173 mg, 0.15 mmol) and the mixture heated at reflux for 5 h. The crude reaction was washed with water and extracted with ethyl acetate. After adding isohexane a dark solid was collected by suction filtration. The solid was adsorbed onto silica and purified by chromatography on silica gel, eluting with isohexane on a gradient of ethyl acetate (20-60%), to give 3-(2-fluoropyridin-5-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (150 mg) as a dark solid: δH (500 MHz, CDCl3) 7.12 (1H, m), 7.30 (1H, d, J 7), 7.99-8.02 (1H, m), 8.10 (1H, s), 8.46 (1H, s), 8.72 (1H, d, J 7); m/z (ES+) 282, 283 (M++H).

Provenance & Evidence