CN(C)C=O.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[N:15][CH:16]=1.[H-].[Na+].F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>O>[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][O:18][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:15][CH:16]=1
To an N,N-dimethylformamide (40 mL) solution of (5-[1,3]dioxolan-2-yl-pyridin-2-yl)-methanol (1.37 g, 7.56 mmol) described in Manufacturing Example 154-1-4 was added sodium hydride (333 mg, 8.32 mmol, 60% in oil), which was stirred for 5 minutes at 0° C. Next, 2-fluoropyridine (716 μL, 8.32 mmol) was added to the reaction mixture, which was stirred for 45 minutes at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1 to 1:1) to obtain the title compound (1.51 g, 77%).
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