[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[Br:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[Br:11])=[O:8]A mixture of 5-bromonicotinoyl chloride 5 (7.5 g, 33 mmol), 2-bromoaniline (5.86 g, 33 mmol) and triethylamine (14 mL, 100 mmol) in anhydrous dichloromethane (100 ml) was stirred under argon overnight. The resulting mixture was worked up with water and extracted with dichloromethane (200 mL×2). The organic phase was collected and dried over Na2SO4. After concentrated to 150 mL, white crystalline solid was crashed out. Filtration and washing with hexanes gave a white solid 6 (10.0 g, 85% yield).
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