HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 71237760, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-5-(trifluoromethyl)pyridine | HCID 2736434 | — |
| Reactant | HCID 71238419 | HCID 71238419 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71237760 | HCID 71237760 | 62.1% |
Reaction Steps
500 mg (R)-4-{(R)-1-[7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinolin-5-yloxy]-ethyl}-pyrrolidin-2-one (325 mg 2-Bromo-5-trifluoromethyl-pyridine, 46 mg Bis(triphenylphosphine)palladium(II) chloride, 1.96 mL 2N aqueous sodium carbonate and 10 mL DMF were heated at 80° C. for 18 hours. The reaction was partitioned between DCM and NaHCO3 (sat aq) then the organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by MPLC using a Hept/EtOAc/MeOH gradient to give 326 mg of (R)-4-{(R)-1-[7-(5-Trifluoromethyl-pyridin-2-yl)-quinolin-5-yloxy]-ethyl}-pyrrolidin-2-one as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199937B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b5e3004ce2fe40289a6458de0bb5bac5 |
| Source note | uspto-grants-2015_12 |