3-Iodo-2-methoxypyridine

1628-89-3

112197-15-6

The general procedure for the synthesis of 3-iodo-2-methoxypyridine using 2-methoxypyridine as starting material was as follows: firstly, [Li(TMP)Zn(tBu)2] was prepared in 0.4 mmol scale THF solution according to the literature method. To this solution, 2-methoxypyridine (0.042 mL, 0.4 mmol) was added and the reaction mixture was stirred at room temperature for 2 h to obtain a light orange solution. Subsequently, the solution was cooled to 0°C and the reaction was quenched with I2 (508 mg, dissolved in 1 mL THF) and stirring was continued for 1 hour. Upon completion of the reaction, 10% Na2S2O3 solution was added until the solution was bleached and the product was extracted with DCM (3 x 1 mL). The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using heptane:DCM (20:80→40:60) as eluent to afford 3-iodo-2-methoxypyridine (2a) as a colorless oil (87.1 mg, 92% yield).1H NMR (400 MHz, CDCl3) δ ppm 4.00 (s, 3H), 6.65 (dd, J = 7.61, 4.88 Hz, 1H), 8.03 (dd, J = 7.61, 1.76 Hz, 1H), 8.13 (dd, J = 4.88, 1.76 Hz, 1H). The data obtained are in agreement with literature reports.