Isobutanol → 2-Bromo-6-(2-methylpropoxy)pyridine

Participants

Reaction Steps

To 2-methylpropan-1-ol (1 mL), was added sodium (36 mg, 1.56 mmol). The mixture was stirred at 70° C. until sodium was ˜75% consumed, then 1 mL THF and the mixture was stirred an additional 15 min. To this mixture, 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 2 h, then was diluted with EtOAc. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 185 mg of Intermediate 162.1 as a colorless oil. LCMS (2 min gradient) RT=1.98 min, 230.2 (M+H)+.

Provenance & Evidence