Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13](C)[C:12]3[N:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:17]([CH2:18][CH3:19])[C:11]=3[C:10](=[O:26])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][CH:28]1[CH2:33][NH:32][CH2:31][CH:30]([CH3:34])[NH:29]1.[CH:35]1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:34][CH:30]1[NH:29][CH:28]([CH3:27])[CH2:33][N:32]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]=[C:12]4[N:15]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:16]=[C:17]([CH2:18][CH3:19])[C:11]4=[C:10]([O:26][CH3:35])[CH:9]=3)=[CH:6][CH:7]=2)[CH2:31]1Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-(4-bromophenyl)-3-ethyl-7-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4(7H)-one (100 mg, 0.24 mmol, 1.00 equiv) in toluene/DMF (2 ml/Id), 2,6-dimethylpiperazine (140 mg, 1.23 mmol, 5.01 equiv), BINAP (15.3 mg, 0.02 mmol, 0.10 equiv), Pd2(dba)3 (22.4 mg, 0.02 mmol, 0.10 equiv), Cs2CO3 (140 mg, 0.73 mmol, 2.96 equiv), dppf (9.18 mg). The resulting solution was stirred overnight at 120° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (200:1-100:1) to yield 6-[4-(3,5-dimethyl-piperazin-1-yl)-phenyl]-3-ethyl-4-methoxy-1-phenyl-1H-pyrazolo[3,4-b]pyridine as a yellow solid.
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