[H-].[Na+].Br[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:6][C:5]=1[F:19].C([Li])CCC.[CH2:25]=[C:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31].C(=O)(O)[O-].[Na+]>O1CCCC1>[F:19][C:5]1[CH:6]=[C:7]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])[CH:8]=[CH:9][C:4]=1[C:27](=[O:31])[C:26]([CH2:30][CH2:29][OH:28])=[CH2:25]136 mg of 60% sodium hydride was added to a tetrahydrofuran (20 ml) solution of 1.0 g of N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide with cooling with ice, and the reaction liquid was stirred at the same temperature for 15 minutes. The reaction liquid was cooled to −78° C., and 1.53 ml of n-butyllithium (2.66 M hexane solution) was dropwise added to it, and the reaction liquid was stirred at the same temperature for 30 minutes. 0.36 ml of 3-methylenedihydrofuran-2 (3H)-one was added to the reaction liquid at the same temperature, and the reaction liquid was stirred at the same temperature for 2 hours, and then heated up to 0° C., and stirred for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction temperature at the same temperature, extracted with ethyl acetate, and the organic layer was washed with saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=3/1) to obtain the entitled compound as a colorless oily substance.
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