[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.[OH2:17].C([O-])([O-])=[O:19].[Na+].[Na+]>CS(C)=O>[C:1]1([C:7](=[O:19])[C:8]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1A solution of 4-(phenylethynyl)pyridine (2.25 g, 12.6 mmol) and powder iodine (1.60 g, 6.3 mmol) in DMSO (30 mL) is heated at 155° C. for 4 h. The reaction mixture is cooled and poured to H2O (100 mL). The aqueous is neutralized with powdered Na2CO3 to pH˜12 and extracted with EtOAc (2×100 mL). The combined organic extracts are washed sequentially with H2O (60 mL) and brine (60 mL), then dried and concentrated. The crude material is purified by chromatography (silica gel: EtOAc/hexane: 20/80) to afford the title compound (0.81 g, 30%) as an oil. MS (+) ES: 212 (M+H)+.
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