HCID 18355197, compound → HCID 18354995, compound

HRID 429620Notes

Reaction equation

HRID 429620 reaction equation
[C:1]1([CH3:29])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([O:21]CC4C=CC=CC=4)=[O:20])[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H][H]>[Pd].CO.O>[C:1]1([CH3:29])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([OH:21])=[O:20])[C:13]=3[CH:12]=[CH:11]2)(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 18355197HCID 18355197, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18354995HCID 18354995, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of benzyl 1-(4-toluenesulfonyl)indole-4-carboxylate (550 mg) and 10% palladium on charcoal (200 mg) in methanol (20 ml) and water (2 ml) was hydrogenated at ambient temperature (an initial hydrogen pressure was set to 3.5 atm.). The theoretical amount of hydrogen was absorbed in 6 hours. The resulting mixture was filtered through a bed of celite and the filtrate was evaporated in vacuo. The residue was diluted with chloroform and the solution was dried over magnesium sulfate. Filtering and removal of solvents afforded a crude product. The crude product was triturated with diethyl ether-n-hexane (1:3) to give 1-(4-toluenesulfonyl)indole-4-carboxylic acid (330 mg) as a brown powder.

Workup

  1. customwas hydrogenated at ambient temperature
  2. customThe theoretical amount of hydrogen was absorbed in 6 hours
  3. filtrationThe resulting mixture was filtered through a bed of celite
  4. customthe filtrate was evaporated in vacuo
  5. additionThe residue was diluted with chloroform
  6. dry with materialthe solution was dried over magnesium sulfate
  7. filtrationFiltering
  8. customremoval of solvents
  9. customafforded a crude product
  10. customThe crude product was triturated with diethyl ether-n-hexane (1:3)

Sources & evidence

ORD record
ord-c7e656eedd9c44fca05a3240efb98c45
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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