[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7](Br)[CH:8]=1)[NH2:5].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[NH:24]1[CH:28]=[CH:27][CH:26]=[N:25]1>CS(C)=O.[Cu]I.O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[C:7]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)[CH:8]=1To a solution of 3,5-dibromoaniline (0.50 g, 1.99 mmol) in DMSO (2.0 mL) was added sequentially L-Proline (0.041 g, 0.36 mmol), Cs2CO3 (1.16 g, 3.58 mmol), CuI (0.038 g, 0.20 mmol) and pyrazole (0.12 g, 1.80 mmol). The reaction mixture was degassed for 10 min and then heated to 110° C. for 48 h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled to room temperature, added water and extracted with ethyl acetate (×3). The combined organics was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 15% EtOAc-Hexane) to get the desired compound (0.18 g, 37%).
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