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

HRID 2394448Notes

Reaction equation

HRID 2394448 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:15]2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 867531375-[1-(4-Benzyloxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione

Product 1

HCID 189734445-[1-(4-Hydroxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedioneYield 50.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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%.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resulting organic phase was washed with a saturated common salt solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7b060c95468d4c6dadb33ba3949873cf
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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