Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 4,4-Dimethyl-2-pyrrolidinone | HCID 637593 | — |
| Reactant | 2,4-Dichloro-5,7-difluoro-3-methylquinoline | HCID 59631040 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59631088 | HCID 59631088 | — |
Reaction Steps
2,4-dichloro-5,7-difluoro-3-methylquinoline (1.50 g, 6.20 mmol), XantPhos (540 mg, 0.93 mmol), 4,4-dimethylpyrrolidin-2-one (700 mg, 6.20 mmol), cesium carbonate (2.80 g, 8.70 mmol), 3 A activated molecular sieves (1.0 g) and Pd2(dba)3 (280 mg, 0.31 mmol) were slurried in 1,4-dioxane (21 mL). The reaction was heated in an oil bath at 100° C. for 1 h. After this time the reaction was cooled to rt, diluted with EtOAc and filtered over a pad of Celite™. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, 0 to 30% EtOAc:DCM as eluant) to give 1-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-4,4-dimethylpyrrolidin-2-one. Mass Spectrum (ESI) m/e=325.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08765940B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-2fdfb30531c548369cc3710e7a4a29fd |
|---|
| Source note | uspto-grants-2014_07 |
|---|
