[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.[CH3:16][NH:17][C:18]([C:20]1[C:24]2[C:25]([CH3:37])([CH3:36])[CH:26](CC)[C:27]3[CH:28]=[N:29][C:30](I)=[N:31][C:32]=3[C:23]=2[N:22]([CH3:38])[N:21]=1)=[O:19].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C)C=O>[CH3:16][NH:17][C:18]([C:20]1[C:24]2[C:25]([CH3:36])([CH3:37])[CH2:26][C:27]3[CH:28]=[N:29][C:30]([NH:15][C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][N:5]5[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]5)[CH:10]=4)=[N:31][C:32]=3[C:23]=2[N:22]([CH3:38])[N:21]=1)=[O:19]Pd(OAc)2 (16.34 mg, 0.0728 mmol), (±)-BINAP (45.33 mg, 0.0728 mmol) and dimethylformamide (12 mL) were charged in a round-bottom flask flushed with argon. The mixture was stirred under argon for 30 minutes. Then 3-(4-methyl-piperazin-1-ylmethyl)-phenylamine (448.4 mg, 2.184 mmol), ethyl 8-iodo-1,4,4-trimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid methylamide (300 mg, 0.728 mmol), K2CO3 (1.508 g, 10.910 mmol) and dimethylformamide (10 mL) were added. The resulting mixture was heated to 80° C. in an oil bath under argon with good stirring for 3 hours. After cooling to room temperature, the reaction mixture was filtered by suction filtration washing with dichloromethane and the filtrate was evaporated to dryness. The crude was purified by flash chromatography on silica gel (eluant; dichloromethane/methanol 95:5) to afford 215 mg (yield 62%) of pure title compound.
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