[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](Br)[CH:8]=1)[NH2:5].[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Cu+2].O>[N:10]1([C:2]2[CH:3]=[C:4]([CH:6]=[C:7]([N:10]3[CH:14]=[CH:13][CH:12]=[N:11]3)[CH:8]=2)[NH2:5])[CH:14]=[CH:13][CH:12]=[N:11]1.[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:8]=1)[NH2:5]The mixture of 3,5-dibromoaniline (1.16 g, 4.6 mmol), pyrazole (0.47 g, 6.9 mmol), Fe(acac)3 (0.35 g, 1.0 mmol), Cu(OAc)2.H2O (0.18 g, 1.0 mmol) and cesium carbonate (3.00 g, 9.2 mmol) in 20 mL DMF was stirred at 135° C. in a sealed tube for 3 days. The mixture was diluted with EtOAc, stirred vigorously, filtered through celite, concentrated in vacuo, subjected to silica flash column to isolate 3,5-di(1H-pyrazol-1-yl)aniline and 3-bromo-5-(1H-pyrazol-1-yl)aniline (0.52 g).
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