C(N(CC)CC)C.Br[C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([Cl:17])=[CH:11][CH:10]=1.[CH2:18]([OH:21])[C:19]#[CH:20].O>[Cu](I)I.C(OCC)(=O)C>[Cl:17][C:12]1[CH:11]=[CH:10][C:9]([C:20]#[C:19][CH2:18][OH:21])=[N:14][C:13]=1[O:15][CH3:16]
Triethylamine (70 mL) and bistriphenylphosphinepalladium(II) dichloride (756 mg) were added to 6-bromo-3-chloro-2-methoxypyridine (12.1 g), 2-propyn-1-ol (4.0 g) and copper iodide (210 mg) in a nitrogen atmosphere, and the mixture was stirred at room temperature for four hours. Water and ethyl acetate were added to the reaction solution, followed by filtration. The aqueous layer was adjusted to pH 3 or less with 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 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=7:3→5:5) to give the title compound as a light brown powder (8.60 g, 80%).
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