Water → 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid

HRID 2264622Notes

Reaction equation

HRID 2264622 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.C([Li])CCC.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1.C(Cl)(Cl)Cl>[C:18]1([S:24]([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:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 69867Indole-3-Carboxylic AcidHCID 178418339Butyllithium

Product 1

HCID 7364841-(phenylsulfonyl)-1H-indole-3-carboxylic acidYield 11.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.8 mg of indole-3-carboxylic acid was dissolved in 1 mL of tetrahydrofuran, 0.042 mL of n-butyllithium (1.58 M hexane solution) was added to the solution at 0° C., the resulting mixture was stirred for 30 minutes. Then 5.3 mg of benzenesulfonyl chloride was added to the mixture, and the resulting mixture was stirred at 0° C. overnight. Water and chloroform were added to the mixture, the organic layer was separated and concentrated under reduced pressure, and the residue was purified by HPLC to obtain 1.0 mg of 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid.

Workup

  1. stirringthe resulting mixture was stirred at 0° C. overnight
  2. customthe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-80173af9f6474ef7ae515118ec545986
Source dataset
uspto-grants-2010_12
Patent number
US07855225B2

Reaction notes

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