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1,4-Dioxane → 2-(2-Ethylsulfanylphenyl)-3-methyl-6-trifluoromethylquinoxaline

HRID 1775255
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HRID 1775255 반응식
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)[CH3:2].Cl[C:20]1[C:29]([CH3:30])=[N:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[N:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C(OCC)(=O)C>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:20]1[C:29]([CH3:30])=[N:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)[N:21]=1)[CH3:2]
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참가 물질

8

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, Tribasic2회HCID 135252492-Chloro-6-(trifluoromethyl)-3-methylquinoxalineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 1182058232-(2-Ethylsulfanylphenyl)-3-methyl-6-trifluoromethylquinoxaline수율 37.2%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

A mixture of 0.52 g of 2-ethylsulfanylphenylboronic acid pinacol ester, 0.40 g of 2-chloro-3-methyl-6-trifluoromethylquinoxaline, 0.02 g of tris(dibenzylideneacetone)dipalladium(0), 0.05 g of 2-dicyclohexylphosphino-2′,6′-dimethoxyphenyl, 0.84 g of tripotassium phosphate and 6 ml of 1,4-dioxane was stirred at 70° C. for 2 hours. 0.30 g of tripotassium phosphate was added to the cooled reaction mixture, and the mixture was stirred under heat-reflux for 3 hours. Ethyl acetate and water were added to the cooled reaction mixture, and the mixture was filtered. The filtrate was extracted with ethyl acetate and then dried over anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.21 g of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethylquinoxaline (Compound of Present Invention 2).

후처리

  1. stirringthe mixture was stirred
  2. temperatureunder heat-reflux for 3 hours
  3. filtrationthe mixture was filtered
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ac08dd0957e74032880053f47b6256c5
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09260436B2

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