[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[O:22][CH:23]=[CH:24][N:25]=1.[NH4+].[Cl-]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]1[O:22][CH:23]=[CH:24][N:25]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]A mixture of 5-nitroindazole (500 mg, 3.07 mmol), potassium carbonate (889 mg, 6.44 mmol) and 2-(chloromethyl)-1,3-oxazole (396 mg, 3.37 mmol) in DMF (3 mL) was stirred for 3 hours at room temperature. Saturated NH4Cl was added and the mixture was extracted with dichloromethane. After evaporation, the residue was purified on silica gel (30 to 35% EtOAc/petroleum ether) to give 5-nitro-1-(1,3-oxazol-2-ylmethyl)-1H-indazole (474 mg, 63%); NMR spectrum (CDCl3) 5.76 (s, 2H), 7.11 (s, 1H), 7.60 (d, 1H), 7.62 (s, 1H) 8.26 (s, 1H), 8.31 (d, 1H), 8.74 (s, 1H).
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