5-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione → 5-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

HRID 1738166Notes

Reaction equation

HRID 1738166 reaction equation
[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:19]3=[O:43])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H][H]>O1CCOCC1.[Pd]>[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:43])=[CH:44][CH:45]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 232983005-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 1540055-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedioneYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.05 g of 5-{4-[2-(indol-1-yl)-ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 14) in 100 ml of dioxane was stirred in an atmosphere of hydrogen and in the presence of 3.1 g of 10% w/w palladium-on-charcoal, first at room temperature for 30 minutes, then at 60° C. for 2 hours and then at 80° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was then purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.06 g of the title compound, melting at 42.3-44.6° C.

Workup

  1. waitat 80° C. for 3 hours
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe concentrate was then purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6b82c05a66714a51b7aaae71de8f3832
Source dataset
uspto-grants-1999_10
Patent number
US05962470

Reaction notes

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