Potassium Phosphate, Tribasic → 3-Cyclopropyl-2-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-2-fluoropyridine (1.56 g, 8.86 mmol), cyclopropylboronic acid (990 mg, 11.5 mmol), potassium phosphate (6.59 g, 31.0 mmol) and tricyclohexylphosphine (249 mg, 0.89 mmol) in a mixed solvent of toluene (40 mL) and water (2 mL) under a nitrogen atmosphere was added palladium(ii) acetate (99.5 mg, 0.443 mmol). The reaction mixture was heated at 100° C. for 3 h. The mixture was allowed to cool to RT, filtered through a pad of Celite™ and washed with EtOAc. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 10% EtOAc in hexane, to provide 3-cyclopropyl-2-fluoropyridine as light-yellow oil.

Provenance & Evidence