Cyclopentanol → 2-Bromo-6-(cyclopentyloxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To cyclopentanol (1 mL), was added sodium (36 mg, 1.56 mmol). When the sodium was consumed, the mixture was diluted with 1 mL THF and 2,6-dibromopyridine (250 mg, 1.06 mmol). The mixture was stirred at 90° C. for 3 h, sodium hydride (20 mg) was added and the mixture was stirred an additional 1 h at 90° C. The reaction 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 222 mg of 159.1 as a colorless oil. LCMS (2 min gradient) RT=2.01 min, 242.15 (M+H)+.

Provenance & Evidence