Potassium Phosphate, Tribasic → 5-Cyclopropylpicolinonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-2-cyanopyridine (1.25 g, 9.02 mmol), cyclopropylboronic acid (1.00 g, 11.7 mmol), potassium phosphate (6.70 g, 31.6 mmol), tricyclohexylphosphine (380 mg, 1.4 mmol), toluene (200 mL), and water (2 mL) under argon was added palladium acetate (150 mg, 0.68 mmol). The mixture was heated at 100° C. overnight and then cooled to rt. The mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was washed with water, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (EtOAc/hexane: 0-50%) to yield a light yellow oil which becomes solid while standing at room temperature.

Provenance & Evidence