2-Methoxyethanol → 5-Bromo-2-(2-methoxyethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of NaH 55% (133 mg, 3.06 mmol) in DME (3 ml) was cooled to 0° C., then 2-methoxyethanol (Aldrich, Buchs, Switzerland, 0.362 ml, 4.58 mmol) was added. The solution was stirred at rt for 15 min. After that 5-bromo-2-chloropyridine (Aldrich, Buchs, Switzerland, 294 mg, 1.528 mmol) was added and the RM was heated by microwaves at 150° C. for 10 min. Then the RM was quenched with saturated aqueous NaHCO3 (50 ml) and extracted with EtOAc (2×). The combined organic layers were washed with brine (2×), dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by MPLC (hexane/EtOAc 0 to 30%). The fractions containing product were evaporated together to give the title compound as a colorless oil. (LC-MS: tR 1.20 min (Method B); M+H=232, 234 (Br-pattern) MS-ES. 1H-NMR (d6-DMSO, 400 MHz) 8.28.8.21 (m, 1H), 7.91-7.84 (m, 1H), 6.86-6.79 (m, 1H), 4.31 (t, 2H), 3.62 (t, 2H), 3.26 (s, 3H))

Provenance & Evidence