To a degassed solution of 2-(2,6-dichloropyridin-3-yl)ethanol (200 mg, 1.04 mmol) and 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (272 mg, 1.04 mmol) in 1,4-dioxane (8 mL) and water (200 μl) was added CS2CO3 (679 mg, 2.08 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium chloride (68 mg, 0.10 mmol) under N2 protection. The resulting mixture was heated to 90° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of the celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. Preparative TLC (eluted with 20% EtOAc/DCM) to provide 2-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)ethanol (60 mg, yield: 19%) MS (M+H)+: 291.
