[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:12][N:11]=[N:10]1.C1C(=O)N([Br:28])C(=O)C1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>CC#N>[Br:28][C:18]1[CH:19]=[C:14]([C:13]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[N:10]=[N:11][N:12]=2)[C:15]([NH2:20])=[N:16][CH:17]=13-(1-(2,3-Difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine was stirred in CH3CN (15 mL) and treated with NBS (2 eq). The reaction mixture was maintained at room temperature for 30 min. The reaction was subsequently poured into sat NaHCO3 solution and treated sequentially with 5 mL Na2S2O3 and 2 mL 6N NaOH. The solids were filtered, washed with water, and dried in vacuo to afford 5-bromo-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine, which was purified by silica gel chromatography. Using the same procedure, 5-bromo-3-(1-(2,3-dichlorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine and 5-bromo-3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine can be produced from 3-(1-(2,3-dichlorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine and 3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine, respectively.
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