Sodium Bicarbonate → 6-(Oxan-4-yl)pyridin-3-amine

Participants

Reaction Steps

After 1.0M toluene-solution (9.8 ml) of lithium bis(trimethylsilyl)amide was added to bis(dibenzylideneacetone)palladium (0) (67 mg) and tri-tert-butylphosphine tetrafluoroborate (118 mg) at 70° C. under an atmosphere of nitrogen, a toluene solution (8.2 ml) of 5-bromo-2-(tetrahydro-2H-pyran-4-yl)pyridine (1.97 g) was added dropwise and stirred at the same temperature for 0.5 hour. Next, the reaction solution was cooled to room temperature, 1.0M tetrahydrofuran-solution (7.0 ml) of tetrabutylammonium fluoride was added and stirred at the same temperature for 1.5 hours. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (1.1 g) as a white solid.

Provenance & Evidence