Potassium Phosphate, Tribasic → HCID 86674202, compound

Participants

Reaction Conditions

Reaction Steps

Combine 5-bromo-2-(difluoromethyl)pyridine (5.00 g, 24.03 mmol), N,O-dimethylhydroxylamine hydrochloride (3.52 g, 36.09 mmol), palladium(II) acetate (0.162 g, 0.722 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.695 g, 1.201 mmol), and potassium phosphate (tribasic) (15.3 g, 72.07 mmol) in m-xylene (50 mL). Purge the reaction vessel with carbon monoxide gas. Heat the solution to 100° C., and stir under an atmosphere of carbon monoxide for 16 hours. Safely purge the vessel in a well-ventilated area with nitrogen until it is free of carbon monoxide. Add water (200 mL) to quench the reaction. Adjust the pH of the mixture to 7 with a saturated sodium bicarbonate aqueous solution. Extract the mixture with EtOAc. Dry the combined organic extracts over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the resulting residue by silica gel chromatography eluting with a 2:1 ratio of petroleum ether to EtOAc to give the title compound (2.5 g, 48% yield) as a clear oil. LCMS (m/z) 216 (M+1).

Provenance & Evidence