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

HRID 1775255Notes

Reaction equation

HRID 1775255 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ac08dd0957e74032880053f47b6256c5
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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