Sodium hydride → HCID 104809848, compound

Participants

Reaction Steps

To a suspension of 60% NaH (640 mg, 16 mmol) in DMF (80 mL) is added tetrahydro-pyran-4-ol (1.6 g, 16 mmol) at 0° C. After the mixture is stirred at room temperature for 0.5 h, 3-bromo-5-bromomethyl-pyridine (1.6 g, 6.4 mmol) is added at 0° C. under N2 atmosphere. The mixture is stirred at room temperature for 16 hrs. Then saturated NH4Cl aqueous solution is used to quench the reaction and the mixture is extracted with DCM. The organic layers are combined, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash column chromatography to give 700 mg of 3-bromo-5-(tetrahydro-pyran-4-yloxymethyl)-pyridine.

Provenance & Evidence