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Potassium Carbonate → 5-ethyl-2-(2'-fluoro-4'-methyl-3'-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide

HRID 2044201
Notes
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Reaction equation

HRID 2044201 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1I.[F:16][C:17]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][C:18]=1[NH:19]C.[C:29]([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]>[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1[NH:19][C:18]1[CH:21]=[CH:22][C:23]([CH3:29])=[C:24]([C:25]([F:28])([F:27])[F:26])[C:17]=1[F:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21938643N,N-dimethyl-5-ethyl-2-iodophenylacetamideHCID 688217352-fluoro-N-methyl-3-(trifluoromethyl)aniline

Product 1

HCID 689983795-ethyl-2-(2'-fluoro-4'-methyl-3'-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalyst
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N,N-dimethyl-5-ethyl-2-iodophenylacetamide (2.0 g, 6.3 mmol), 2-fluoro-methyl-3-trifluoromethylaniline (2.4 g, 12.6 mmol), copper (0.2 g, 3.2 mmol), cuprous iodide (0.6 g, 3.2 mmol), and K2CO3 (0.9 g, 6.3 mmol) in xylenes (6.0 mL) are heated at reflux for 24 h. After cooling, the crude reaction mixture is diluted with EtOAc and filtered through Celite®. The filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography, eluting with hexanes, then up to 25% EtOAc/hexane mixtures to give the target compound 5-ethyl-2-(2′-fluoro-4′-methyl-3′-trifluoromethylanilino)phenylacetic acid N,N-dimethyl amide.

Workup

  1. temperatureare heated
  2. temperatureat reflux for 24 h
  3. temperatureAfter cooling
  4. customthe crude reaction mixture
  5. filtrationfiltered through Celite®
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by flash chromatography
  8. washeluting with hexanes

Sources & evidence

ORD record
ord-b988099f036c4bb8993d28c8e4a56da5
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08586782B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes