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

HRID 646218
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HRID 646218 반응식
[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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 5946Tetraethylammonium Chloride
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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 1 N 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)−.

후처리

  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 1 N 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)

출처 및 근거

ORD 기록
ord-5a656aec50794ea6aa61595e8cbcddd9
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705030B2

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