A vial was charged with 1-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.075 g, 0.234 mmol), (4-chlorophenyl)boronic acid (0.040 g, 0.257 mmol), Pd(Ph3P)4 (0.027 g, 0.023 mmol), and potassium carbonate (0.097 g, 0.701 mmol). The vial was flushed with Ar (g), then 1,4-dioxane (0.877 ml) and Water (0.292 ml) were added in sequence. The vial was sealed and microwaved at 100° C. for 30 minutes. (3-fluorophenyl)boronic acid (0.065 g, 0.468 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (4.80 mg, 0.012 mmol), and chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(ii) dichloromethane (8.86 mg, 0.012 mmol) were added and the reaction was microwaved at 100° C. for 45 minutes. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 12 g, gradient elution 0-10% MeOH:DCM) to afford 1-(3′-fluoro-[1,1′-biphenyl]-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=8.74 (d, J=5.8 Hz, 1H), 8.70 (br. s., 1H), 8.58 (br. s., 1H), 8.23 (d, J=9.1 Hz, 2H), 8.13 (d, J=5.5 Hz, 1H), 8.03 (d, J=9.3 Hz, 1H), 7.92 (d, J=8.3 Hz, 2H), 7.80 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.0 Hz, 2H), 7.60-7.51 (m, 2H), 7.30-7.20 (m, 2H), 7.15-6.97 (m, 1H). m/z (ESI) 457.2 (M+H)+.
