A mixture of 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.24 g, 3.27 mmol), 3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-iodo-benzoic acid (1.65 g, 3.27 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (66 mg, 0.08 mmol) in dimethylacetamide (20 mL) and aqueous solution of sodium carbonate (2M, 4.9 mL) was stirred at 100° C. for 14 h. The cooled reaction mixture was poured into 150 mL of water acidified with 6 N hydrochloric acid and filtered. The solids were redissolved in a mixture of dichloromethane and ethanol and filtered again. The filtrate was concentrated and the brown residue was purified by flash silica gel chromatography using a gradient of a solution of 90 parts ethyl acetate, 10 parts methanol, and one part acetic acid and hexanes afforded 1.5 g of a light brown solid (2.38 mmol, 76% yield). MS: m/z 630 [MH+]
