Hydrochloric Acid → 1-Methyl-6-oxo-1,6-dihydropyridine-3-boronic Acid

Participants

Reaction Conditions

Reaction Steps

5-Bromo-1-methylpyridin-2(1H)-one (400 mg, 2.17 mmol), tricyclohexylphosphine (72 mg, 0.26 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (540 mg, 2.17 mmol), potassium acetate (522 mg, 5.32 mmol) and Pd2(dba)3 (97 mg, 0.11 mmol) were added to a flask. The flask was evacuated and purged with argon three times. Fully degassed dioxane (9.5 mL) was added and the reaction was sealed and heated at 90° C. overnight. The mixture was then cooled to room temperature, filtered over a thin layer of celite, eluting with dichloromethane. The majority of the dichloromethane was evaporated under reduced pressure and hexane was added until a precipitate formed. The slurry was filtered and the filtrate was concentrated. The resulting residue was dissolved in dioxane, 10 equivalents of 1 N hydrochloric acid were added, and the mixture was stirred overnight. Removal of the solvent under reduced pressure and purification of the resulting residue via reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) afforded the title compound.

Provenance & Evidence