Potassium Carbonate → HCID 71087598, compound

Participants

Reaction Steps

Under an atmosphere of nitrogen, a solution of 6-bromo-pyridine-2-carboxylic acid (CAN: 21190-87-4, 1 g, 4.9 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Example 9-d, 1.1 g, 5.4 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 0.08 g, 0.1 mmol) and potassium carbonate (1.37 g, 10 mmol) in water (50 mL) was stirred for 24 h at 100° C. The reaction mixture was extracted with ethyl acetate (50 mL), the pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (6×50 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by prep-HPLC to yield the title compound (0.3 g, 1.5 mmol, 29.5%) as white solid; MS (EI): m/e=206.1 [M+H]+.

Provenance & Evidence