Hydrochloric Acid → (5-(Benzyloxy)-6-(trifluoromethyl)pyridin-3-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(benzyloxy)-5-bromo-2-(trifluoromethyl)pyridine (Intermediate G25.2, 521 mg, 1.569 mmol) in dry 1,4 dioxane (10 ml), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (438 mg, 1.726 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (344 mg, 0.471 mmol) and potassium acetate (462 mg, 4.71 mmol) were added and the suspension was stirred at 90° C. overnight. Then, HCl 4 N was added (10 mL) and the solution was stirred overnight. The solvent was removed under reduced pressure and crude was purified by C18 flash chromatography Snap 30 g eluent ((H2O/ACN)) 95:5+0.1% HCOOH}:{(ACN/H2O) 95:5+HCOOH 0.1%} from 95:5 to 0:100 affording the title compound (400 mg, 1.347 mmol, 86% yield) a white solid.

Provenance & Evidence