Iodobenzene diacetate → 5-Bromo-3-methyl-[1,2,3]triazolo[1,5-a]pyridine

Participants

Reaction Steps

To a stirring solution of (Z)-4-bromo-2-(1-hydrazonoethyl)pyridine (2.53 g, 11.8 mmol) in DCM (40 mL) was added (diacetoxyiodo)benzene (3.8 g, 11.8 mmol) in small portions over several minutes and stirred at room temperature for 45 minutes. The reaction was quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (40 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 45% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=6.9 Hz, 2H), 7.79 (s, 2H), 6.97 (d, J=6.5 Hz, 2H), 2.57 (s, 7H).

Provenance & Evidence