Ammonia → HCID 23725206, compound

Participants

Reaction Steps

To a mixture of 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (112.6 mg, 0.5 mmol) containing [Cu(OH).TMEDA]2Cl2 (23.2 mg, 0.05 mmol) in dry methanol (5 mL) was added 4-fluorophenylboronic acid (140 mg, 1.0 mmol) under an air atmosphere and the resulting mixture stirred at room temperature overnight. After this time, concentrated ammonia solution (2 mL) was added and then the resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate. The organic extracts were then dried over sodium sulphate and evaporated. Purification by preparative HPLC on reversed phase eluting with an acetonitrile/water [0.1% aq NH3 (25%)] gradient afforded the title compound (34 mg, 21%) which was obtained as a white solid. MS (ESI): m/e=320.0 [M+H]+.

Provenance & Evidence