HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-(5-Chloro-2-cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Bromocyclopentane | HCID 8728 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(5-Chloro-2-hydroxy-pyridin-3-yloxy)-6,7-dimethoxyquinoline | HCID 178486808 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(5-Chloro-2-cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinoline | HCID 23078406 | 62% |
Reaction Steps
4-(5-Chloro-2-hydroxy-pyridin-3-yloxy)-6,7-dimethoxyquinoline (39 mg) was suspended in N,N-dimethylformamide (7 ml). Cyclopentyl bromide (0.3 ml) and potassium carbonate (300 mg) were added to the suspension, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (29 mg, yield 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07560558B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-d6516d28e80f43e291a2e572673659f7 |
| Source note | uspto-grants-2009_07 |