[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O.[OH-].[K+].Cl.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=1>CN(C=O)C>[Br:13][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[N:8]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[N:7]=14-Nitro-1H-indazole (1.0 g, 6.1 mmol) and N-bromosuccinimide (1.1 g, 6.4 mmol) were mixed with anhydrous DMF (10 mL) in a 20 mL vial. The reaction was stirred at ambient temperature for 5 minutes. KOH (1.1 g, 18.3 mmol) and 2-(chloromethyl)-6-methylpyridine hydrochloride (1.4 g, 7.6 mmol) were added to the vial and the reaction mixture was stirred for 18 hours. The product was precipitated from solution by addition of H2O (10 mL) to the reaction mixture. The solids were collected vacuum filtration, washed with H2O and dried under vacuum to afford 3-bromo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (1.7 g).
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