Potassium Phosphate, Tribasic → 3-(3-Methyl-3H-imidazol-4-yl)-phenylboronic acid

Participants

Reaction Conditions

Reaction Steps

1,3-Benzenediboronic acid (300 mg, 1.8 mmol), 5-bromo-1-methylimidazole (291 mg, 1.8 mmol), potassium phosphate (1.15 g, 5.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (164 mg, 0.18 mmol), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (142 mg, 0.36 mmol) were combined with DMA (3 mL) in a sealed tube purged with N2. The reaction was heated at 130° C. for 25 min in a microwave reactor. The solution was diluted with MeOH, filtered, and concentrated in vacuo. Purification by preparatory HPLC gave 166 mg (45%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 7.91-7.98 (m, 2H), 7.83 (s, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 3.83 (s, 3H). [M+H] calc'd for C10H11BN2O2, 202; found, 202.

Provenance & Evidence