3-Hydroxypyridine → HCID 89581172, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(5-bromopyridin-2-yl)ethanol (600 mg, 3.00 mmol), pyridin-3-ol (283 mg, 2.98 mmol) and triphenyl phosphine (1.54 g, 5.88 mmol) was stirred in anhydrous tetrahydrofuran (20 mL) under nitrogen atmosphere. After stirring for 1 hour, the mixture was cooled to 0° C. Diisopropyl azodicarboxylate (658 mg, 3.26 mmol) was added dropwise and the reaction was stirred at room temperature for 18 hours. Then the solvent was evaporated and the residue was purified by column chromatography (silica gel, pure ether) to 5-bromo-2-(1-(pyridin-3-yloxy)ethyl)pyridine (744 mg, 89%). 1H NMR (300 MHz, CD3OD): δ 8.63-8.62 (m, 1H), 8.21-8.19 (m, 1H), 8.08-8.06 (m, 1H), 7.98-7.94 (m, 1H), 7.45 (d, J=5.1 Hz, 1H), 7.33-7.28 (m, 2H), 5.51 (q, J=6.3 Hz, 1H), 1.68 (d, J=6.3 Hz, 3H).

Provenance & Evidence