Potassium Phosphate, Tribasic → 2-(6-(7-(Trifluoromethyl)imidazo[1,2-a]pyrimidin-3-yl)pyridin-2-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 3-(6-bromopyridin-2-yl)-7-trifluoromethyl-imidazo[1,2-α]pyrimidine (200 mg, 0.58 mmol), 2-cyanophenylboronic acid (172 mg, 1.16 mmol) and potassium phosphate (370 mg, 1.75 mmol) in N,N-dimethylacetamide (4 ml) was added tetrakis(triphenylphosphine)paladium(0) (33.8 mg, 29.2 μmol) and the reaction heated at 80° C. for 18 h. After cooling to ambient temperature the reaction was poured onto a cartridge of strong cation-exchange resin and non-basic impurities removed by elution with methanol. The product was then eluted with a 2M solution of ammonia in methanol and evaporated to give an orange oil. This residue was purified by silica gel chromatography eluting with isohexane on a gradient of ethyl acetate (20-60%) to give a solid. Crystallisation from ethyl acetate-dichloromethane gave 2-[6-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)pyridin-2-yl]benzonitrile (26 mg) as a white solid: δH (400 MHz, CDCl3) 7.38 (1H, d, J 7),7.61 (2H, m), 7.78 (2H, m), 7.91 (2H, m), 7.99 (1H, dd, J 9 and 9), 8.58 (1H, s), 10.62 (1H, d, J 9); m/z (ES+) 366 (M++H).

Provenance & Evidence