Sodium hydride → 4-Bromo-2-[(oxan-4-yl)oxy]pyridine

Participants

Reaction Steps

To a suspension of NaH (0.4 g, 10 mmol) in THF (20 ml) at 0° C. was added 4-hydroxytetrahydropyran (1.02 ml, 10 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 30 mins before 4-bromo-2-chloropyridine (0.89 ml, 8.0 mmol) was added dropwise. The reaction mixture was stirred for 18 h before being quenched with EtOH (1 ml), partitioned between CH2Cl2 and H2O and extracted CH2Cl2 (×2). The organics were combined, dried (MgSO4), filtered and the solvent removed in vacuo. Purified by column chromatography to afford 4-Bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine MS: [MH]+ 258, 260

Provenance & Evidence