[H-].[Na+].Cl[C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1.Br[CH2:19]B1OC(C)(C)C(C)(C)O1.F.[Na]>O.O1CCCC1>[CH3:17][O:16][C:9]1[CH:8]=[CH:7][C:6]2[N:5]=[C:4]3[CH2:19][O:15][CH2:14][C:13]3=[CH:12][C:11]=2[CH:10]=1
To the mixture of sodium hydride (61%, 250 mg, 6.4 mmol) and tetrahydrofuran (25 ml), (2-chloro-6-methoxy-quinolin-3-yl)-methanol (1.4 g, 6.4 mmol) synthesized in Example 16 was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at room temperature for 40 minutes. To the reaction mixture, 2-(bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (92%, 700 mg, 2.9 mmol) synthesized in Production Example 2 was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at 50° C. (an outer temperature) for 5 hours. After cooling the reaction mixture to 0° C. (an outer temperature), sodium hydrogen fluoride (580 mg, 9.3 mmol) was added to the reaction mixture at the same temperature, followed by the dropwise addition of water (20 ml) at the same temperature. After stirring the reaction mixture for 15 minutes at room temperature, the solvents were evaporated under reduced pressure. Acetone was added to the obtained residue, followed by filtration, and the solvents were evaporated under reduced pressure from the filtrate. Ethyl acetate was then added to the obtained residue, followed by filtration, and the solvents were evaporated under reduced pressure from the filtrate. The mixed solvent of ethyl acetate-diethyl ether (1:4) was added to the obtained residue, followed by filtration. The crystals precipitated in the filtrate were collected, thereby obtaining the entitled compound (260 mg). The solvents were evaporated under reduced pressure from the filtrate, and ethyl acetate was added to the obtained residue and then heated to 60° C., resulting in the precipitation of crystals. The crystals were collected, thereby obtaining the entitled compound (250 mg (510 mg in total), 53%).
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