Cesium carbonate → HCID 17978962, compound

Participants

Reaction Conditions

Reaction Steps

2-(Imidazo[1,2-α]pyrimidin-7-yl)-2-methylpropionitrile (100 mg, 0.51 mmol), 2-(6-bromopyridin-2-yl)benzonitrile (159 mg, 0.61 mmol) and cesium carbonate (332 mg, 1.02 mmol) were suspended in 1,4-dioxane and degassed with nitrogen for 20 min. Tetrakis(triphenylphosphine)-palladium(0) (29 mg, 0.025 mmol) was added and the mixture was heated at 80° C. for 3 h. The reaction was cooled to ambient temperature then diluted with water (60 ml) and extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with brine (70 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a pale yellow oil. The oil was purified by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%). Collecting appropriate fractions followed by recrystallisation from ethyl acetate/isohexane gave 2-{6-[7-(1-cyano-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile (70 mg, 38%) as a white solid: δH (360 MHz, CDCl3) 1.86 (6H, s), 7.43 (1H, d, J 7), 7.59-7.63 (2H, m), 7.80 (2H, m), 7.86-7.97 (3H, m), 8.42 (1H, s), 10.44 (1H, d, J 7); m/z (ES+) 365 (M++H).

Provenance & Evidence