Boron tribromide → HCID 53379902, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(biphenyl-3-yl)-5,6-dimethoxypyridine-3-carbonitrile (17 mg, 0.054 mmol) in CH2Cl2 (1 mL) was added BBr3 solution (1 M in CH2Cl2, 0.537 mL) and stirred at 45° C. for 19 h. The reaction mixture was concentrated and the residue was stirred in 3 N aqueous HCl for 30 min. The precipitated white solid was collected by filtration and purified by preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA) to give 2 mg (13%) of 2-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-3-carbonitrile as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.89 (s, 1H), 7.81 (d, J=7.2 Hz, 1H), 7.70 (d, J=7.6 Hz, 2H), 7.65-7.58 (m, 2H), 7.47 (t, J=7.6 Hz, 2H), 7.38 (t, J=7.4 Hz, 1H) 1 6.96 (s, 1H). High resolution mass spec (FT/ICR) calc (M+H)+=289.0972 found 289.0969.

Provenance & Evidence