Water → HCID 86593496, compound

HRID 854497Notes

Reaction equation

HRID 854497 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1.[F:21][C:22]([F:32])([F:31])[O:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O.[Cu]Br.C(OCC)(=O)C>[F:21][C:22]([F:31])([F:32])[O:23][C:24]1[CH:29]=[CH:28][C:27]([N:15]2[C:16]3[C:12](=[CH:11][C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:9][CH:8]=4)=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 10286124HCID 10286124, compound

Product 1

HCID 86593496HCID 86593496, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 0.6 g (2.6 mmol) 5-(4-trifluoromethoxy-phenyl)-1H-indole, 0.53 mL (2.8 mmol) 4-(trifluoromethoxy)iodobenzene, 0.075 g (0.52 mmol) copper(I) bromide and 0.54 g (3.9 mmol) K2CO3 in 10 mL anhydrous N-methylpyrrolidinone was heated to reflux overnight with stirring. The reaction was allowed to cool and was then poured into 200 mL of water. The aqueous solution was shaken with 200 mL ethyl acetate, the combined aqueous and organic phases were filtered, and the organic phase was separated. The aqueous phase was extracted once more with 200 mL ethyl acetate and the combined organic phases were washed with brine and concentrated. The crude product was chromatographed on silica (5–7% EtOAc-hexane as elutant) to afford 0.505 g (44% yield) of 1,5-bis-(4-trifluoromethoxy-phenyl)-1H-indole.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureto cool
  4. filtrationthe combined aqueous and organic phases were filtered
  5. customthe organic phase was separated
  6. extractionThe aqueous phase was extracted once more with 200 mL ethyl acetate
  7. washthe combined organic phases were washed with brine
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on silica (5–7% EtOAc-hexane as elutant)

Sources & evidence

ORD record
ord-afc8605e788c46b58832c41f8e01e78d
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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