A mixture of 4-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 3.3 mmol), 2-(5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (0.8 g, 3.3 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (133 mg, 0.2 mmol) in THF/Acetonitrile/saturated NaHCO3 (20 ml/20 ml/20 ml) was stirred at 70° C. overnight. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (2×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2-{5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]pyridine-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (1.3 g, 85% yield). 1H NMR (500 MHz, DMSO-d6) δ 0.05 (s, 9H), 0.92 (t, 2H), 2.95 (d, 6H), 3.62 (t, 2H), 5.68 (s, 1H), 6.77 (s, 1H), 7.96, (s, 1H), 7.98 (s, 1H), 8.41 (s, 1H), 8.71 (s, 1H), 8.72 (s, 1H). MS: m/z 461.3 (M+H+).
