Potassium Phosphate, Tribasic → HCID 90203845, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2,4-dichloro-pyridine (CAN 849937-4, 4 g, 17.63 mmol), potassium phosphate tribasic (11.21 g, 52.89 mmol), cyclopropylboronic acid (5.2 g, 35.84 mmol) in toluene (45 ml) and water (5 ml) was degassed with argon for 15 minutes. To this reaction mixture was added palladium (II) acetate (80 mg, 0.35 mmol) and tricyclohexylphosphine (0.487 g, 1.74 mmol) at 25° C. and reaction mixture was again purged with argon for 5 minutes. The reaction mixture was then stirred at 100° C. for 12 hours. The reaction mixture was cooled to 25° C. and the catalyst was filtered off through a pad of celite and the filter pad was washed with ethyl acetate (3×50 ml). The filtrate was washed with brine, dried over sodium sulfate and evaporated to dryness. The crude material was purified by flash chromatography on silica eluting with a gradient of heptane and ethyl acetate to yield the title compound (2 g, 61%) as a light yellow oil. MS (ESI, m/z): 188.2 (M+H+).

Provenance & Evidence