Diethyl Ether → HCID 10271181, compound

Participants

Reaction Steps

2′-Fluoro-5′-(7-formylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (100 mg), tosylmethyl isocyanide (60 mg) and potassium carbonate (40 mg) were suspended in methanol (10 ml) and heated at reflux for 90 min. The reaction was cooled, diluted with dichloromethane and filtered. The filtrate was evaporated to dryness and the residue partitioned between dichloromethane and water. The organic phase was dried over anhydrous magnesium sulfate, filtered and pre-adsorbed onto silica. Purification by flash column chromatography on silica gel eluting with dichloromethane with 1% ammonia on a gradient of methanol (1-5%) gave a solid. Trituration with diethyl ether afforded 2′-fluoro-5′-[7-(oxazol-5-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile as a yellow solid (40 mg, 34%): δH (360 MHz, DMSO) 7.53 (1H, d, J 7), 7.65 (1H, s), 7.70 (1H, s), 7.81 (1H, s), 7.87-7.95 (3H, m), 8.06 (1H, d, J 8), 8.11 (1H, s), 8.20 (1H, s), 8.70 (1H, s), 9.19 (1H, d, J 7); m/z (ES+) 382 (M++H).

Provenance & Evidence