Nitrogen → 3-[3-([1,2,4]Triazol-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-7-trifluoromethylimidazo[1,2-a]pyrimidine (139 mg, 0.53 mmol), the foregoing boronate ester (269 mg, 1.05 mmol) and K3PO4 (483 mg, 2.1 mmol) in DMA (3 ml) was degassed with a stream of N2 for 5 min and then tetrakis(triphenylphosphine)palladium(0) (60 mg, 10 mol %) was added and the reaction heated at 65° C. for 70 min. EtOAc (100 ml) was added and the mixture washed with H2O (3×100 ml) and brine (100 ml), dried (MgSO4) and concentrated under reduced pressure while dry loading onto silica. The residue was purified by column chromatography on silica using 5% MeOH in dichloromethane to yield 3-[3-([1,2,4]triazol-4-yl)phenyl]-7-trifluoromethylimidazo[1,2-a]pyrimidine (70 mg, 40%), which was then recrystallised from EtOAc/isohexanes: δH (400 MHz, d6-DMSO) 7.55 (1H, d, J 7.2), 7.70-7.90 (3H, m), 8.16 (1H, s), 8.39 (1H, s), 9.24 (2H, s), 9.48 (1H, d, J 7.2); m/z (ES+) 331 (M+H+).

Provenance & Evidence