N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-nitro-benzenesulfonamide → 3-Amino-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:31][CH3:32])=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)(=[O:21])=[O:20])[CH:17]=1)=[CH:5]2>C(O)(=O)C.[Zn]>[NH2:28][C:24]1[CH:23]=[C:22]([S:19]([NH:18][C:16]2[CH:17]=[C:12]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=4)[CH:13]=[CH:14][C:15]=2[O:31][CH3:32])(=[O:20])=[O:21])[CH:27]=[CH:26][CH:25]=1Participants
4
Procedure
The product from Example 15 (0.388 g, 0.84 mmol) was taken up in glacial acetic acid (25 mL), and zinc dust (2.8 g, 325 mesh) was added in portions over 3 minutes and was then stirred 2 hours at room temperature. The zinc was filtered off and washed with ethyl acetate and tetrahydrofuran. The organic solution was concentrated to dryness, the residue partitioned between ethyl acetate (200 mL) and sodium bicarbonate solution (200 mL), the organic layer washed with brine and dried (magnesium sulfate), filtered, concentrated, and the resulting solid triturated with hexanes/ethyl acetate, 3/1, v/v and the insoluble portion collected by filtration to give the product as a faintly yellow solid (0.296 g), mp 235-238° C.