HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 1-(5-Bromo-3-pyridinyl)-2-pyrrolidinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Pyrrolidone | HCID 12025 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-(5-Bromo-3-pyridinyl)-2-pyrrolidinone | HCID 68619460 | 44.2% |
Reaction Steps
Cesium carbonate (213 mg), pyrrolidin-2-one (45 mg), Xantphos (76 mg), and Pd2(dba)3 (60 mg) were added to a 1,4-dioxane (4 ml) solution containing 3,5-dibromopyridine (100 mg) in a nitrogen atmosphere, followed by reflux for 4 hours. The reaction mixture was adjusted to room temperature and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 1:1), and a white solid of 1-(5-bromopyridin-3-yl)pyrrolidin-2-one (45 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895585B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-117c135a6fd74339ac2a33d72b24d8e9 |
| Source note | uspto-grants-2014_11 |