Potassium Carbonate → HCID 10082475, compound

HRID 230738Notes

Reaction equation

HRID 230738 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 249055-BromoindoleHCID 742994-Chlorophenylboronic acid

Product 1

HCID 10082475HCID 10082475, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred slurry of 6.35 g (60 mmol) K2CO3, 2.94 g (15 mmol) 5-bromoindole, 2.50 g (16 mmol) 4-chlorophenylboronic acid, and 0.48 g (0.42 mmol) tetrakistriphenylphosphine palladium was heated to reflux for 2½ hours. The reaction mixture was allowed to cool and was then poured into 200 ml water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated. The residue was chromatographed on silica to afford 1.39 g 5-(4-chlorophenyl)indole as a white solid.

Workup

  1. temperatureto reflux for 2½ hours
  2. temperatureto cool
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-75d7d7a51610442abfff9757f6bd2aca
Source dataset
uspto-grants-2009_07
Patent number
US07566791B2

Reaction notes

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