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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1750055Generated: November 2, 2026

Toluene → 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

https://huagongshe.com/reaction/1750055

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium CarbonateHCID 11430—
Reactant1-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzeneHCID 118035563—
Reactant3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridineHCID 118035578—
CatalystTriphenylphosphineHCID 11776—
CatalystCupric acetate monohydrateHCID 165397—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridineHCID 11803561190.3%

Reaction Steps

A mixture of 0.11 g of 3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine, 0.15 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene, 0.01 g of palladium(II) acetate, 0.01 g of triphenylphosphine, 0.02 g of copper(II) acetate monohydrate, 0.13 g of potassium carbonate and 3 ml of toluene was stirred under heating and refluxing for 2 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 0.20 g of 2-(2-ethylsulfanyl-4-trifluoromethylsulfanylphenyl)3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as Compound 7).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09156838B2
Source datasetuspto-grants-2015_10
ORD IDord-f86d8bbd09d64d1f88924f79388f1c15
Source noteuspto-grants-2015_10