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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629319Generated: October 27, 2026

Ethyl Acetate → HCID 118468364, compound

https://huagongshe.com/reaction/629319

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium BicarbonateHCID 516892—
ReactantRac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-oneHCID 118468159—
ReactantHCID 178478124HCID 178478124—
CatalystHCID 178418851HCID 178418851—
SolventTetrahydrofuranHCID 8028—
ProductHCID 118468364HCID 118468364—

Reaction Steps

To a solution of rac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-one (0.23 g) in THF (3.0 mL) were added ((6-chloropyridin-3-yl)methyl)zinc(II) chloride (3.66 mL) and bis(tri-tert-butylphosphine)palladium(0) (0.07 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr under argon atmosphere. To the reaction mixture were added 5% aqueous sodium bicarbonate and ethyl acetate, the mixture was stirred, and the insoluble substance was removed by filtration. The filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.15 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315458B2
Source datasetuspto-grants-2016_04
ORD IDord-8a625d899a974308940e79148d13e733
Source noteuspto-grants-2016_04