Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | 2-Bromobutane | HCID 6554 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo- | HCID 2786702 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 117770038 | HCID 117770038 | 48% |
Reaction Steps
To a mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (500 mg), cesium carbonate (2.17 g), potassium iodide (553 mg) N,N-dimethylformamide (10 mL) and 1,2-dimethoxyethane (10 mL) was added 2-bromobutane (776 mg) at room temperature, and the mixture was stirred overnight at 60° C. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted threetimes with ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (330 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09085578B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-9d34407f90f241f1a9266b80a887fca7 |
|---|
| Source note | uspto-grants-2015_07 |
|---|