Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Bromocyclopropane | HCID 78037 | — |
| Reactant | HCID 178493808 | HCID 178493808 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89586444 | HCID 89586444 | — |
Reaction Steps
To a solution of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (1.0 g) in DMF (20 ml) were added cesium carbonate (2.429 g), bromocyclopropane (0.597 ml) and sodium iodide (0.559 g) at room temperature. The reaction mixture was stirred at 150° C. for 30 hr in an autoclave, allowed to cool to room temperature, and poured into water (100 ml). The mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate). The fraction containing the title compound was purified again by silica gel column chromatography (NH, methanol/ethyl acetate), and crystallized from methanol/ethyl acetate to give the title compound (15 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150588B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-14385af22bea48b5adc452b665fa841a |
|---|
| Source note | uspto-grants-2015_10 |
|---|