Methyl iodide → 5-Bromo-3-isopropoxy-2-methoxymethyl-pyridine

Participants

Reaction Steps

To a solution of (5-bromo-3-isopropoxy-pyridin-2-yl)-methanol (stage 190.1.2, 0.61 mmol) in DMF (3 ml) was added 55% NaH in oil (0.688 mmol) was added. The RM was stirred for 30 min at rt then was added iodomethane (0.684 mmol). The RM was stirred for 2.5 h at rt then was quenched with MeOH and purified by preparative HPLC. The fractions containing product were combined, basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a yellow oil. (HPLC: tR 2.83 min (Method A); M+H=260, 262 MS-ES).

Provenance & Evidence