[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[N:10]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:9]=2)[CH2:4][CH2:3]1.C(O)(=O)C>C(O)C.[Zn]>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[N:10]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:9]=2)[CH2:6][CH2:7]1Zinc (3.28 g, 50.46 mmol) was added to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1-(phenylsulfonyl)-1H-indole (2 g, 5.04 mmol) in ethanol (500 mL). Acetic acid (30 mL) was then added dropwise with stirring while the reaction was cooled in a ice water bath. The resulting solution was stirred for 2 hours at room and then filtered. The filtrate cake was washed with ethanol, and the collected filtrate was concentrated in vacuo. The residue was purified by column chromatography using a 10:1 methanol/ammonia solvent system to afford 1 g (54%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indol-5-amine as a yellow solid.
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