Potassium Iodide → 2-Iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine

Participants

Reaction Steps

To a solution of 5-(4-methoxyphenyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine (825 mg, 3.43 mmol) and p-toluene sulphonic acid (1.77 g, 10.3 mmol) in acetonitrile (40 mL) was added a solution of potassium iodide (1.42 g, 8.55 mmol) and sodium nitrite (474 mg, 6.87 mmol) in water (2 mL) at 24° C. After 18 h, ethyl acetate was added to the reaction mixture. The resulting solution was washed with water (2×) and saturated aqueous sodium chloride solution. The organic was dried over magnesium sulfate, filtered, and concentrated. Purification using ISCO CombiFlash (2→5% methanol in dichloromethane) afforded 2-iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine (950 mg, 71%). 1H NMR (400 MHz, CDCl3), δ: 7.90 (d, 2H), 7.64 (m, 1H), 7.57 (t, 1H), 7.05 (t, 3H); ES-MS m/z 351.9.

Provenance & Evidence