[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:25])[CH2:11][C:12]1[CH:17]=[C:16](Cl)[C:15]([N+:19]([O-])=O)=[CH:14][C:13]=1[N+:22]([O-])=O)[CH3:8].C(O)(=O)C>ClCCl.[Zn]>[CH2:7]([O:9][C:10](=[O:25])[CH2:11][C:12]1[CH:17]=[C:16]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:15]([NH2:19])=[CH:14][C:13]=1[NH2:22])[CH3:8]Piperidine (120 mg) was added to a solution of (5-chloro-2,4-dinitro-phenyl)-acetic acid ethyl ester (150 mg) in dichloromethane (5 mL) and the resulting mixture was stirred at room temperature for 10 minutes. Glacial acetic acid (0.3 mL) and zinc dust (1 scoop) were added and the reaction mixture was stirred at room temperature for 20 minutes. The resulting mixture was filtered through a CELITE™ pad, the filter cake was washed with dichloromethane and the filtrate was evaporated under reduced pressure. The residue was then diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give (2,4-diamino-5-piperidin-1-yl-phenyl)-acetic acid ethyl ester. This material was dissolved in toluene (2.5 mL) and heated at 150° C. in a microwave reactor for 10 minutes. The reaction mixture was then cooled, evaporated under reduced pressure and the residue was purified by flash chromatography (DCM/MeOH, 95/5) to give 30 mg of 6-amino-5-piperidin-1-yl-1,3-dihydro-indol-2-one. MS=232 [M+H]+.
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