[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Br:10])[CH:5]=[C:4]([F:11])[C:3]=1[NH:12][C:13](=[O:15])[CH3:14].[H-].[Na+].Br[CH2:19]/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([Br:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]([CH2:19]/[CH:20]=[CH:21]\[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13](=[O:15])[CH3:14]To the solution of 8-6 (1.3 g, 3.82 mmol) in THF (20 mL) at room temperature was added NaH (100 mg, 4.2 mmol, dispersed in mineral oil, 60%). The mixture was stirred for 30 min until no gas was released. (E)-ethyl 4-brombut-2-enoate (0.88 g, 4.58 mmol) in THF (5 mL) was added. The mixture was stirred overnight at room temperature. TLC showed that the reaction was completed. Water was added to the reaction mixture and extracted with ethyl acetate (50 mL×3). The combined organic layers were combined and were concentrated in vacuo. The residue was purified by flash chromatography (silica gel, elution with ethyl acetate/petroleum=1:8 to 1:2) to afford 8-7 (1.6 g, 92.4%) as yellow oil.
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