Boron tribromide → 5-[1-(4-Hydroxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione

Participants

Reaction Steps

There was dissolved, in 30 ml of methylene chloride, 259 mg of 5-[1-(4-benzyloxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione prepared in Example 265 and the resulting solution was cooled to -78° C. After dropwise addition of a solution of boron tribromide (1.0M) in methylene chloride (10.17 ml), the temperature of the mixture was slowly raised up to room temperature. After stirring the mixture for 2 hours, a saturated sodium hydrogen carbonate aqueous solution was added followed by extraction with ethyl acetate. The resulting organic phase was washed with a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give 105 mg of 5-[1-(4-hydroxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 51%.

Provenance & Evidence