[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([O-:8])=[O:7].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][S:2]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:17][CH:16]=2)[CH:12]=[N:13]1)(=[O:4])=[O:3]
Methanesulfonyl chloride (887 μl, 7.20 mmol) was added to a suspension of 5-nitroindazole (979 mg, 6.00 mmol) and triethylamine (2.0 ml, 14.3 mmol) in dichloromethane (20 ml) at 0° C., and the resulting mixture was stirred at room temperature for 3 hours. Methanesulfonyl chloride (222 μl, 1.80 mmol) was further added thereto, followed by stirring for another 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution to terminate the reaction, followed by extraction with chloroform. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by washing with methanol to obtain 1-(methylsulfonyl)-5-nitro-1H-indazole (1.16 g, 80%).
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