[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]#[C:11][CH2:12][OH:13])=[N:6][C:7]=1[O:8][CH3:9].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[I:28]N1C(=O)CCC1=O.Cl>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:10](/[I:28])=[CH:11]/[CH2:12][OH:13])=[N:6][C:7]=1[O:8][CH3:9]A solution of 3-(5-chloro-6-methoxypyridin-2-yl)prop-2-yn-1-ol (3.0 g) in tetrahydrofuran (50 mL) was stirred under ice-cooling in a nitrogen atmosphere, during which a solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al(R)) in toluene (3.6 M, 7 mL) was added dropwise thereto. The mixture was stirred at room temperature for one hour. The reaction solution was cooled to an external temperature of −78° C. A solution of N-iodosuccinimide (6.2 g) in tetrahydrofuran (30 mL) was added dropwise and then the mixture was stirred at an external temperature of −78° C. for one hour. 1 M hydrochloric acid was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was sequentially washed with a 10% sodium thiosulfate solution and brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→5:5) to give the title compound as a brown powder (3.79 g, 76%).
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