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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1804279Generated: October 31, 2026

Cesium carbonate → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-one

https://huagongshe.com/reaction/1804279

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant(R)-4-Methyloxazolidin-2-oneHCID 2734858—
ReactantDi-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneHCID 11953610—
Reactant3-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-oneHCID 54755234—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-oneHCID 5848468940.8%

Reaction Steps

To a mixture of 3-{5-chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one (207 mg) described in Preparation Example 120, (R)-4-methyloxazolidin-2-one (50.6 mg) described in Preparation Example 25, cesium carbonate (228 mg), tris(dibenzylideneacetone)dipalladium (0) chloroform (51.8 mg) and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (24 mg) was added toluene (1 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporation of the solvent, the residue was purified by column chromatography (ethyl acetate:methanol) to give the title compound (97.5 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354401B2
Source datasetuspto-grants-2013_01
ORD IDord-0f2902769d224430a57c6049c9f2f48a
Source noteuspto-grants-2013_01