[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[N:27][CH:28]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:22][C:23]2[CH:28]=[N:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:3]=1To a solution of 3-iodo-4-nitro-1H-indazole (3.0 g, 10.4 mmol) in DMF (25 mL) was added potassium carbonate (2.87 g, 20.8 mmol) at ambient temperature. After 15 minutes, 5-(chloromethyl)-2-methylpyridine hydrochloride (2.03 g, 11.4 mmol) was added. The mixture was allowed to stir at ambient temperature for 18 hours. The mixture was concentrated under reduced pressure and diluted with ice-water (300 mL). The precipitated solids were collected by filtration and washed with water to provide 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (3.77 g, 92% yield).
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