1,1'-Carbonyldiimidazole → 8-methoxy-2H,3H-(1,2,4)triazolo(4,3-a)pyridin-3-one

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To a stirred solution of (3-methoxypyridin-2-yl)hydrazine (2.7 g, 19.4 mmol) in THF (70 mL) was added 1,1′-carbonyldiimidazole (15.75 g, 90.1 mmol) at RT. After 16 hours, the resultant solid was collected by filtration and washed with THF. The solid was dissolved in a mixture of MeOH (120 mL) and water (20 mL) and stirred at RT for 10 minutes before evaporating to dryness. The resultant residue was subjected to flash chromatography (SiO2, gradient 3 to 5% MeOH in CHCl3) to afford the title compound (2.81 g, 88%) as a white solid. LCMS (Method A): RT=2.08 min, [M+H]+=166.

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