5-Bromo-4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (916 mg, 2 mmol), 2-methoxyphenyl boronic acid (321 mg, 2.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (74 mg, 0.1 mmol), and 2 mL of 2M Na2CO3 (aq) were dissolved in 10 mL of acetonitrile and 10 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 (452 mg, 1.02 mmol, 51% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.74 (s, 1H), 7.37 (m, 1H), 7.23 (dd, J=7.5 Hz, J2=1.5 Hz, 1H), 7.05 (dd, J=8 Hz, J2=1 Hz, 1H), 6.98 (td, J=7.5 Hz, J2=1 Hz, 1H), 5.63 (s, 2H), 3.67 (s, 3H), 3.56 (t, J=8 Hz, 2H), 0.82 (t, J=8 Hz, 2H), −0.09 (s, 9H). MS: m/z 467.1/469.1 (M+H+).
