Boron tribromide → HCID 53379903, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(biphenyl-3-yl)-5,6-dimethoxypyridine-2-carbonitrile (34 mg, 0.107 mmol) in CH2Cl2 (1 mL) was added BBr3 solution (1 M in CH2Cl2, 2.149 mL) and stirred at 50° C. for 21 h. The reaction mixture was concentrated and the residue was stirred in 3 N aqueous HCl. After 1 h, this mixture was concentrated and purified by preparative HPLC (5-60% CH3CN/H2O over 20 min, 0.05% added TFA) to give 17 mg (55%) of 3-(biphenyl-3-yl)-5-hydroxy-6-oxo-1,6-dihydropyridine-2-carbonitrile as a light pink solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.65 (m, 2H), 7.65-7.53 (m, 3H), 7.47 (t, J=8.0 Hz, 3H), 7.39 (t, J=7.6 Hz, 1H), 7.12 (s, 1H). LC/MS (M+H)+ 289.2.

Provenance & Evidence