[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>CC#N>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1)([O-:17])=[O:16]Pyrrolidine (3.89 g, 54.8 mmol) is added to a mixture of 8.40 g (36.5 mmol) of 1-(2-bromoethyl)-4-nitrobenzene and 6.14 g (73.0 mmol) of NaHCO3 in 60 mL of CH3CN at 0° C. The mixture is stirred for 0.5 h at 0° C. and then at 25° C. overnight. The reaction is filtered, the insoluble material is washed with CH3CN and the filtrate and wash were combined. Darco is added, the solution is dried (MgSO4) and evaporated to a viscous red oil. Stirring this material with Et2O caused crystallization of the product. It is collected, washed with Et2O and dried in vacuo to give 7.60 g (95%) of a tan hygroscopic solid. 1H NMR (DMSO-d6) δ 8.22 (d, 2H, J=6.57 Hz), 7.62 (d, 2H, J=6.57 Hz), 3.47 (m, 2H), 3.25 (m, 2H), 3.10 (m, 4H), 1.94 (m, 4H); MS (ESI) m/z 221.2 (M+1).
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