Combine N-(4-Fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (300 mg, 0.56 mmol), 2-Fluoro-3-boronic acid-pyridine (140 mg, 1.12 mmol), CsF (170 mg, 1.12 mmol) and Dichlorobis(triphenylphosphine)palladium (100 mg, 0.14 mmol) in dioxane (2.0 mL) and water (0.200 mL). Evacuate the reaction and place under a nitrogen atmosphere. Heat the resulting reaction in an 80 degree oil bath for 15 h. Cool the reaction and filter through a short pad of silica gel with additional ethyl acetate. Evaporate and purify by flash column chromatography (EtOAc/Hexanes) to yield 141 mg of an off white foam (50%) LRMS: MH+ 503.92.
