Potassium Carbonate → HCID 15322476, compound

HRID 2370982Notes

Reaction equation

HRID 2370982 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11](S(C3C=CC=CC=3)(=O)=O)[CH:10]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 671088721-(Benzenesulfonyl)-3-(4-methoxyphenyl)-1H-indole

Product 1

HCID 15322476HCID 15322476, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-methoxyphenyl)-1-(phenylsulfonyl)-1H-indole (200 mg, 0.55 mmol) and 15 eq potassium carbonate were dissolved in 40 ml MeOH under nitrogen. The mixture was heated at reflux for 16 h, cooled to rt and then concentrated to dryness. DCM and brine were added and the mixture was acidified (pH 2-4) with 2 M HCl. The aqueous layer was extracted with DCM and the combined organic layers were concentrated. The crude product was purified on silica (EtOAc/n-Heptane, 1:1). 121.1 mg 3-(4-methoxyphenyl)-1H-indole was obtained as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated to dryness
  4. additionDCM and brine were added
  5. extractionThe aqueous layer was extracted with DCM
  6. concentrationthe combined organic layers were concentrated
  7. customThe crude product was purified on silica (EtOAc/n-Heptane, 1:1)

Sources & evidence

ORD record
ord-30da9de4dcab48769cc54ec00e892a15
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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