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

HRID 521656
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 521656
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, Tribasic2×HCID 135252492-Chloro-6-(trifluoromethyl)-3-methylquinoxalineHCID 1237879692-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 1182058232-(2-Ethylsulfanylphenyl)-3-methyl-6-trifluoromethylquinoxalineAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8b1cc537d00646cbab0955e1bae89625
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328121B1

Notizen zur Reaktion

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