Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:29]2[CH:33]=[C:32](B(O)O)[CH:31]=[N:30]2)[CH:26]=[CH:27][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>O>[Cl:22][C:23]1[CH:24]=[C:25]([N:29]2[CH:33]=[C:32]([C:2]3[C:11]4[C:6](=[CH:7][C:8]([S:12]([NH:15][C:16]5[CH:21]=[CH:20][N:19]=[CH:18][N:17]=5)(=[O:14])=[O:13])=[CH:9][CH:10]=4)[CH:5]=[CH:4][N:3]=3)[CH:31]=[N:30]2)[CH:26]=[CH:27][CH:28]=1A vial was charged with 1-chloro-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (Intermediate GG) (53 mg, 0.17 mmol), (1-(3-chlorophenyl)-1H-pyrazol-4-yl)boronic acid (44 mg, 0.200 mmol), Pd(AmPhos)2Cl2 (12 mg, 0.017 mmol), potassium phosphate (106 mg, 0.500 mmol), dioxane (1.042 μl), and water (0.347 μl). The vial was sealed and heated in an oil bath overnight at 100° C. The crude reaction mixture was purified using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 μm column with a gradient 5-95% acetonitrile and water with 0.1% ammonium hydroxide modifier to yield 1-(1-(3-chlorophenyl)-1H-pyrazol-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide. m/z (ESI) 463.0 (M+H)+.
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