C([O:4][CH2:5][C:6]([CH3:23])([CH3:22])[CH2:7][N:8]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:21])(=O)C.[CH:24]1([NH:27][C:28](=[O:46])[C:29]2[CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:32]([CH3:44])=[C:31]([F:45])[CH:30]=2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.O>[CH:24]1([NH:27][C:28](=[O:46])[C:29]2[CH:34]=[C:33]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[C:9](=[O:21])[N:8]([CH2:7][C:6]([CH3:22])([CH3:23])[CH2:5][OH:4])[CH:17]=[C:16]4[CH:18]=[O:19])[C:32]([CH3:44])=[C:31]([F:45])[CH:30]=2)[CH2:25][CH2:26]1A solution of 3-(6-bromo-4-formyl-1-oxoisoquinolin-2(1H)-yl)-2,2-dimethylpropyl acetate (Example 1e, 0.25 g) in DMF (10 mL) was treated with N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.28 g), Pd-118 (0.024 g) and potassium carbonate (0.31 g) under nitrogen. The resulting mixture was stirred at 70° C. for 6 h. Methanol (10 mL) was added and stirred at room temperature for 1 h. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (300 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution with 100% ethyl acetate) to afford the subtitle compound (0.30 g) as an oil.
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