5-Bromo-4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (500 mg, 1.02 mmol), 2-(tert-Butoxymethyl)phenylboronic acid (224 mg, 1.05 mmol), dichlorobis(triphenylphosphine)palladium(II) (42 mg, 0.05 mmol), and 1 mL of sodium carbonate solution (2M, 2 mmol) were dissolved in 5 mL of acetonitrile and 5 mL of THF under an atmosphere of nitrogen. The mixture was heated at 60° C. with rapid stirring under N2 for 2 h. Sodium sulfate was added to the reaction mixture and the slurry was filtered over Celite and concentrated. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford the title compound (66 mg, 0.12 mmol, 12% yield).
