Thiazolidinedione → HCID 73473934, compound

HRID 2394404Notes

Reaction equation

HRID 2394404 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=O)[C:4]=2[CH:3]=[CH:2]1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].N1CCCCC1.[S:33]1[CH2:37][C:36](=[O:38])[NH:35][C:34]1=[O:39]>C(#N)C.C(O)C.C(OCC)C>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[C:9]3[C:4](=[C:5]([CH:10]=[C:37]4[S:33][C:34](=[O:39])[NH:35][C:36]4=[O:38])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 73473934HCID 73473934, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
52 °C

Procedure

There were dissolved, in 20 ml of acetonitrile, 2.00 g of indole-4-carbaldehyde and 5.20 g of 4-fluorobenzyl bromide, followed by addition of 9.52 g of potassium carbonate and stirring for 16 hours while heating the reaction mixture to 52° C. The reaction solution was cooled down to room temperature, followed by removal of potassium carbonate through filtration and removal of the solvent through evaporation under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give a yellow oily substance. The substance was dissolved in 40 ml of ethanol, followed by addition, to the solution, of 240 mg of piperidine and 3.4 g of 2,4-thiazolidinedione and reflux of the mixture with heating over 22 hours. The reaction mixture was cooled in an ice bath followed by addition of 80 ml of diethyl ether, stirring at that temperature for one hour, then separation of the precipitated yellow crystals through filtration and washing with diethyl ether to give 3.95 g of 5-[1-(4-fluorobenzyl)indol-4-yl]methylene-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 81%.

Workup

  1. temperatureThe reaction solution was cooled down to room temperature
  2. customfollowed by removal of potassium carbonate through filtration and removal of the solvent through evaporation under reduced pressure
  3. customThe resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=10:1)
  4. customto give a yellow oily substance
  5. temperaturereflux of the mixture
  6. temperaturewith heating over 22 hours
  7. temperatureThe reaction mixture was cooled in an ice bath
  8. stirringstirring at that temperature for one hour
  9. customseparation of the precipitated yellow crystals
  10. filtrationthrough filtration
  11. washwashing with diethyl ether

Sources & evidence

ORD record
ord-1bb40381d9454d678f19308fd5e5d832
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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