[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][N:14]([CH2:22][CH2:23]Cl)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[H-].[Na+]>CN(C)C=O>[C:9]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:23][CH2:22][N:14]([C:15]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:21])[CH2:13][CH2:12]1)#[N:10]2-(4-Fluorophenyl)acetonitrile (1.35 g, 10.0 mmol) and tert-butyl bis(2-chloroethyl)carbamate (2.42 g, 10.0 mmol) were combined in dimethylformamide (30 mL) and cooled to 0° C. The reaction was treated with sodium hydride (760 mg, 30.0 mmol) in several portions. The ice bath was removed and the reaction heated at 60° C. for 24 h. After cooling to room temperature, the mixture was poured into ice water and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (15% ethyl acetate/hexanes) gave 1.65 g (54%). 1H-NMR (CDCl3, 500 MHz) δ 7.39-7.44 (m, 2H), 7.04-7.10 (m, 2H), 4.23-4.27 (m, 2H), 3.12-3.21 (m, 2H), 2.03-2.07 (m, 2H), 1.82-1.92 (m, 2H), 1.45 (s, 9H). Mass spec.: 327.11 (MNa)+.
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