[CH:1]12[N:7]([C:8]3[CH:9]=[CH:10][C:11]([N+:20]([O-])=O)=[C:12]([C:14]#[C:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:13]=3)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2>C(O)(=O)C.O.CO.[Zn]>[CH:1]12[N:7]([C:8]3[CH:9]=[CH:10][C:11]([NH2:20])=[C:12]([C:14]#[C:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH:13]=3)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]23-[5-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine (75 mg, 0.25 mmol) was dissolved in a mixture of glacial acetic acid (940 μL) and water (230 μL). Zn dust (164 mg, 2.51 mmol) was added at room temperature. The solution was stirred for 10 min. The reaction was diluted with methanol (5 mL), filtered and concentrated. The residue was dissolved in ethyl acetate, washed with 50% saturated NaHCO3 (2×20 mL) and brine, dried over Na2SO4, filtered, and dried down to a light orange solid. Purification by silica gel chromatography (5-15% methanol/dichloromethane) provided 4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(3-(dimethylamino)prop-1-ynyl)aniline as a light orange oil (20 mg, 30% yield). LC/MS m/z 270.5 [M+H]+.
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