[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]#[N:14])([O-:3])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(N(C)C)=O>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:13]#[N:14])=[N:8]15-nitro-1H-indazole-3-carbonitrile (150 mg, 0.797 mmol) was taken up in DMA (4 mL) and K2CO3 (331 mg, 2.392 mmol) was added, followed by dropwise addition of MeI (0.060 mL, 0.957 mmol). The reaction was stirred at rt overnight. The reaction mixture was quenched with a saturated solution of NaHCO3 and Na2S2O3, then diluted with EtOAc. The organic layer was washed with sat'd NaHCO3, then brine, and dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography eluting with 0%-50% EtOAc/Hex. 1-methyl-5-nitro-1H-indazole-3-carbonitrile (134 mg) was obtained as a yellow solid.
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