[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1.Cl[C:19]1[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.CO.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].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:19]2[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=2)[N:6]=1Under argon, 130 mg (0.58 mmol) of 3-(2-fluorobenzyl)-1H-indazole from example 5A, 84 mg (0.58 mmol) of 6-chloro-1,3,5-triazine-2,4-diamine, 11 mg (0.011 mmol) of tris(dibenzylidene-acetone)dipalladium, 16 mg (0.034 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 262 mg (0.80 mmol) of cesium carbonate are introduced into 4 ml of degassed toluene and heated at 90° C. for 20 h. The mixture is then diluted with ethyl acetate and methanol, filtered and concentrated in vacuo. The residue is purified by preparative HPLC to result in 36 mg (19% of theory) of the title compound. In addition, 65 mg of the starting compound are recovered.
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