Sodium Carbonate → 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

To a glass microwave vial was added 3-bromo-2-fluoropyridine (4.6132 g, 26.2 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.88 g, 32.8 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (1.472 g, 2.097 mmol), and sodium carbonate (13.89 g, 131 mmol) in DME (41.9 mL) and water (10.49 mL) to stir at 80° C. overnight. Upon completion, the reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with water, sat NaCl, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine. MS (ESI, pos. ion) m/z: 180.1.

Provenance & Evidence