Water → HCID 59596797, compound

HRID 2264623Notes

Reaction equation

HRID 2264623 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.S([O-])(O)(=O)=O.[K+].O>C1COCC1.[Li]CCCC.CCCCCC>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]2)(=[O:23])=[O:22])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 69867Indole-3-Carboxylic AcidHCID 516920Potassium bisulfate

Product 1

HCID 59596797HCID 59596797, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418244HCID 178418244, compoundSolvent

Procedure

To a solution of 300 mg of 1H-indole-3-carboxylic acid in 9 mL of THF, 2.68 mL of 1.60 M n-BuLi hexane solution was added dropwise while the inner temperature was kept at −50° C. or lower by cooling in a dry ice-acetone bath, and the resulting mixture was stirred at the same temperature for 5 minutes, then at 0° C. for 1 hour. The solution was cooled in a dry ice-acetone bath and a solution of 461 mg of 4-methoxybenzenesulfonyl chloride in 1 mL of THF was added dropwise. The solution was stirred at 0° C. for 3 hours. To the solution, 20 mL of 5% aqueous potassium hydrogen sulfate solution and 40 mL of water were added in this order, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. To the residue was added 5 mL of ethyl acetate, and the resulting mixture was stirred at room temperature for 15 minutes. The white crystals formed were collected by filtration to obtain 509 mg of 1-[(4-methoxyphenyl)sulfonyl]-1H-indole-3-carboxylic acid as a white solid.

Workup

  1. customwas kept at −50° C.
  2. temperaturelower by cooling in a dry ice-acetone bath
  3. waitat 0° C. for 1 hour
  4. temperatureThe solution was cooled in a dry ice-acetone bath
  5. stirringThe solution was stirred at 0° C. for 3 hours
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionTo the residue was added 5 mL of ethyl acetate
  11. stirringthe resulting mixture was stirred at room temperature for 15 minutes
  12. customThe white crystals formed
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8d9dedd426964d4c98bcf586d220f09f
Source dataset
uspto-grants-2010_12
Patent number
US07855225B2

Reaction notes

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