[Si:1]([O:8][C:9]1[C:10]([C:15]2[CH:16]=[C:17]([N+:21]([O-])=O)[CH:18]=[CH:19][CH:20]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.[Pd]>[Si:1]([O:8][C:9]1[C:10]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[NH2:21])=[N:11][CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]A suspension of 3-(3-tert-butyldimethylsilyloxypyridin-2-yl)-nitrobenzene (332 mg) in ethanol (5 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 150 mg) under a hydrogen atmosphere for 4 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 3-(3-tert-butyldimethylsilyloxypyridin-2-yl)aniline (303 mg).
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