Sodium Carbonate → 1-Benzenesulfonyl-3-phenylindole

HRID 1868420Notes

Reaction equation

HRID 1868420 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Cl-].[NH4+]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27762153-Bromo-(1-phenylsulfonyl)indole

Product 1

HCID 111103941-Benzenesulfonyl-3-phenylindoleYield 47%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 500 mg (1.5 mmol) of 1-benzenesulfonyl-3-bromo-1H-indole, 245 mg (2.0 mmol) of phenylboronic acid, 42 mg (0.04 mmol) of Pd[(Ph3P)]4 in 10 mL of toluene, 5 mL of ethanol, and 3 mL of 2 M aqueous sodium carbonate solution was warmed at reflux overnight. The mixture was then cooled and diluted with 15 mL of saturated aqueous ammonium chloride solution and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 10 mL portions of saturated aqueous ammonium chloride solution and 10 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed onto silica gel and chromatographed on silica gel eluting with ethyl acetate-hexanes (2:98) to afford 235 mg (47%) of 1-benzenesulfonyl-3-phenyl-1H-indole.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux overnight
  3. temperatureThe mixture was then cooled
  4. extractionextracted with three 15 mL portions of ethyl acetate
  5. washThe combined organic layers were washed with three 10 mL portions of saturated aqueous ammonium chloride solution and 10 mL of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel eluting with ethyl acetate-hexanes (2:98)

Sources & evidence

ORD record
ord-1dd59c6060f04d00bf46967a55f1a07b
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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