O[CH2:2][CH2:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.S(Cl)(Cl)=O.[Na].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].[I-].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.O>[N:12]1[CH:11]=[CH:10][N:9]2[C:4]([CH2:3][CH2:2][N:20]3[C:21](=[O:23])[CH2:22][S:18][C:19]3=[O:24])=[CH:5][CH:6]=[CH:7][C:8]=12
To a suspension of 4.0 g (24.7 mmol) of 5-(2-hydroxyethyl)imidazo[1,2-a]pyridine in 30 ml of chloroform, 5 ml (68 mmol) of thionyl chloride was added. After refluxing for 2 hours, the solvent was distilled off. To a suspension of the residue and 8.36 g (60 mmol) of 2,4-thiazolidinedione sodium salt in 50 ml of N,N-dimethylformamide, 3.75 g (25 mmol) of sodium iodide was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added. The reaction mixture was then extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/1→1/4) to yield 1.00 g (15.5%, light orange powder) of the desired product.
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