HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-{2-[4-(1-Hydroxy-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Carbonyl bromide | HCID 79057 | — |
| Reactant | 5-(5-Methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one | HCID 86695554 | — |
| Reactant | 2-Bromo-1-[4-(1-hydroxy-ethyl)-2-methyl-phenyl]ethanone | HCID 86695558 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-{2-[4-(1-Hydroxy-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one | HCID 86695559 | — |
Reaction Steps
To a solution of 5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 9b, 2.00 g, 8.58 mmol) in DMSO (20 mL) is added cesium carbonate (5.59 g, 17.2 mmol) and the mixture is stirred 10 min at room temperature. Then 2-bromo-1-[4-(1-hydroxy-ethyl)-2-methyl-phenyl]-ethanone (preparation 10b, 2.21 g, 8.58 mmol) is added in portions and the mixture is stirred overnight at room temperature. An additional 0.5 g of the bromoketone is added and the mixture is stirred for 3 h at room temperature. After addition of water, the reaction mixture is extracted with ethyl acetate. The combined organic layer is dried over MgSO4 and evaporated under reduced pressure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08933079B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-b678d557e671473ca6346aa6898a6262 |
| Source note | uspto-grants-2015_01 |