Dichloromethane → HCID 86753140, compound

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Reaction Steps

To 10 ml of methylene chloride, there were dissolved 150 mg of 5-[1-(2-hydroxy-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 323 and 45 mg of triethylamine under an argon gas atmosphere and then 51 mg of methanesulfonyl chloride was added to the solution under ice-cooling. After stirring at room temperature for 30 minutes, 30 ml of ethyl acetate was added to the solution, the mixture was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The resulting residue was dissolved in 10 ml of dimethylformamide, followed by addition of 21 mg of lithium chloride and heating to 70° C. with stirring for 20 hours. The solution was poured into a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (20 ml×3). The resulting extract was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1) to give 35 mg of 5-[1-(2-chloro-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 22%.

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