N1C=CC=CC=1.Br[CH:8](Br)[C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:24])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[N:13][CH:14]=1.[CH2:26]([OH:29])[CH2:27][OH:28].[BH4-].[Na+]>CCOCC.C(O)C.O>[F:23][C:17]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=1[CH:15]([OH:24])[C:12]1[CH:11]=[CH:10][C:9]([CH:8]2[O:29][CH2:26][CH2:27][O:28]2)=[CH:14][N:13]=1To a pyridine solution (60 ml) of the 5-dibromomethyl-2-(2,5-difluorobenzoyl)pyridine (Compound A) (3.91 g, 10 mmol) obtained in Referential Example 20 was added ethylene glycol (6.2 g, 100 mmol). While heating at 90° C., the resulting mixture was stirred for 17 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was dissolved in ether (200 ml). The resulting solution was washed with water, a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was dissolved in ethanol (60 ml). To the resulting solution was added sodium borohydride (190 mg, 5 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. After the addition of water, the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=5:1 to 1:1) to give the title compound (1.52 g, 52%) as an oil.
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