Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.O>C(Cl)Cl>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:26][CH2:25]1To a solution of crude 1-(bromomethyl)-2-(trifluoromethyl)-4-nitrobenzene (13.7 mmol, 60% pure) in CH2Cl2 (20 mL) was added Et3N (1.5 g, 15 mmol) and 4-methylpiperazine (1.5 g, 15 mmol). After stirring for 5 hrs at rt, 50 mL H2O was added, and the mixture was extracted with 50 mL CH2Cl2. The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluent: 10% MeOH in CH2Cl2) to give the product (67.4%, 2.8 g). 1H NMR (300 MHz, CDCl3) δ: 8.52 (1H, s), 8.37-8.40 (1H, d, J=9.0 Hz), 8.00-8.03 (1H, d, J=9.0 Hz), 3.85 (2H, s), 3.09-3.15 (2H, m), 2.90-2.93 (2H, m), 2.80-2.83 (2H, m), 2.67 (3H, s), 2.53-2.59 (2H, m).
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