[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:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1>CN(C=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([I:1])=[N:3]2)=[N:24][CH:25]=1To a solution of 3-iodo-4-nitro-1H-indazole (1.0 g, 3.46 mmol) in DMF (20 mL) was added potassium carbonate (0.956 g, 6.92 mmol) and 2-(chloromethyl)-5-fluoropyridine hydrochloride (0.630 g, 3.46 mmol). The mixture was stirred at ambient temperature for 18 hours under nitrogen. The mixture was concentrated under vacuum and then diluted water (300 mL). The precipitated solids were collected by filtration and washed with water. The material was dried under high vacuum for 16 hours to give 1-((5-fluoropyridin-2-yl)methyl)-3-iodo-4-nitro-1H-indazole (0.968 g).
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