[CH2:1]([Zn]CC)[CH3:2].FC(F)(F)C(O)=O.ICI.[F:16][C:17]([F:35])([F:34])[C:18]([N:20]1[CH2:26][C:25](=[CH2:27])[C:24]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:23]=2[CH2:22][CH2:21]1)=[O:19]>ClCCl>[F:35][C:17]([F:16])([F:34])[C:18]([N:20]1[CH2:26][CH:25]([CH:27]2[CH2:2][CH2:1]2)[C:24]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:23]=2[CH2:22][CH2:21]1)=[O:19]A solution of diethyl zinc (1 mL, 1 M in hexanes) in dichloromethane (1 mL) at 0 C was treated with trifluoroacetic acid in dichloromethane (0.5 mL) and the mixture stirred for 15 min. Diiodomethane (0.280 g, 1.0 mmol) in dichloromethane (0.5 mL) was then added and stirred for 15 minutes. N-Trifluoroacetyl-7-methoxy-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine (0.075 g, 0.26 mmol) in dichloromethane (1 mL) was added and the mixture stirred for 30 minutes at 0 C and then for 2 hours at 20 C. The product mixture was quenched with aqueous saturated NH4Cl (5 mL), extracted to twice with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3 (10 mL), washed with H2O (10 mL), and concentrated. Flash chromatography (7% EtOAc in hexanes, silica) resulted in 0.050 g of a white solid. MS calculated for C15H16F3NO2+H: 300, observed: 300.
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