Cl[Sn]Cl.Cl.[C:5]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)([CH3:8])([CH3:7])[CH3:6].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:5]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[NH2:17])([CH3:8])([CH3:7])[CH3:6]A mixture of SnCl2 (0.364 g, 4 eq), 1.44 mL of HCl 1M and 5 mL of THF was added to a solution of tert-butyl({[2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl})amine (0.147 g, 0.48 mmol) in 20 mL of THF. The reaction mixture was refluxed for 3 h and allowed to cool to room temperature. A saturated aqueous solution of Na2CO3 was added. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (DCM/MeOH/NH4OH//85/15/1) to yield expected compound as a brown oil (65 mg, 49% yield).
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