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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1775255Generated: October 31, 2026

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

https://huagongshe.com/reaction/1775255

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DioxaneHCID 31275—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant2-Chloro-6-(trifluoromethyl)-3-methylquinoxalineHCID 13525249—
Reactant2-(2-(Ethylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 123787969—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product2-(2-Ethylsulfanylphenyl)-3-methyl-6-trifluoromethylquinoxalineHCID 11820582337.2%

Reaction Conditions

Temperature70 °C

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09260436B2
Source datasetuspto-grants-2016_02
ORD IDord-ac08dd0957e74032880053f47b6256c5
Source noteuspto-grants-2016_02