Boron tribromide → 3-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenol

Participants

Reaction Steps

Boron tribromide (1 M in DCM, 13.1 mL, 13.1 mmol) was added slowly to a stirred solution of 3-(3-benzyloxy-phenyl)-6-bromo-[1,2,4]triazolo[4,3-a]pyridine (1 g, 2.63 mmol) in DCM (5 mL) at −78° C. The reaction was allowed to warm up to RT, stirred for 24 h, and treated with sat. NaHCO3 solution until pH>7. The product was extracted with DCM:MeOH 9:1 (mL), dried (MgSO4), and concentrated in vacuo. Purification of the crude residue by FCC (DCM:MeOH, 1:0 to 9:1) afforded the title compound (350 mg, 46%) as a yellow solid. LCMS (Method 2): Rt 2.65 min, m/z 290 and 292 [MH+].

Provenance & Evidence