HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (R)-4-Methyloxazolidin-2-one | HCID 2734858 | — |
| Reactant | Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphane | HCID 11953610 | — |
| Reactant | 3-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one | HCID 54755234 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-one | HCID 58484689 | 40.8% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354401B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-0f2902769d224430a57c6049c9f2f48a |
| Source note | uspto-grants-2013_01 |