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Potassium Carbonate → 1-(3-bromophenyl)-2-[1-(2,2,2-trifluoroethyl)-1H-pyrrol-3-yl]ethane-1,2-dione

HRID 2220440
Notes
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Reaction equation

HRID 2220440 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[C:9]([C:11]2[CH:15]=[CH:14][NH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.CC1C=CC(S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[N+](CC)(CC)(CC)CC.[Cl-].O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:16])[C:9]([C:11]2[CH:15]=[CH:14][N:13]([CH2:28][C:29]([F:32])([F:31])[F:30])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 597726681-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione

Product 1

HCID 597726671-(3-bromophenyl)-2-[1-(2,2,2-trifluoroethyl)-1H-pyrrol-3-yl]ethane-1,2-dioneYield 159.9%

Reagents, catalysts & solvents 4

HCID 5946
Tetraethylammonium Chloride
Catalyst
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione (93 mg, 0.33 mmol) in DMF (5.0 mL) was added 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (170 mg, 0.66 mmol), K2CO3 (100 mg, 0.73 mmol) and Et4NCl (5.5 mg, 0.033 mmol) at room temperature. After heating at 80° C. for 3 days, the reaction mixture is cooled, diluted with H2O, EtOAc. The two layers are separated and the aqueous layer is extracted with EtOAc. The combined organic extracts are washed with 1N HCl aqueous H2O, brine, dried (MgSO4) and concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane: 20/80) to give the title compound (190 mg, 65%) as a solid. mp: 105-106° C. MS (+) ES: 418 (M+CH3COO)−.

Workup

  1. temperaturethe reaction mixture is cooled
  2. customThe two layers are separated
  3. extractionthe aqueous layer is extracted with EtOAc
  4. washThe combined organic extracts are washed with 1N HCl aqueous H2O, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material is purified by chromatography (silica gel, EtOAc/hexane: 20/80)

Sources & evidence

ORD record
ord-8785eccea5fc4714a37bffcbe5038283
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07417047B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes