HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 6-[6-(3,4-Difluoro-phenoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3,4-Difluorophenol | HCID 75927 | — |
| Reactant | 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline | HCID 24968367 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 6-[6-(3,4-Difluoro-phenoxy)-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl]-quinoline | HCID 59320278 | 34.5% |
Reaction Steps
A solution of 6-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (60 mg, 0.203 mmol, 1.0 equiv.), 3,4-difluorophenol (0.223 mmol, 1.1 equiv.), Cs2CO3 (86 mg, 0.264 mmol, 1.3 equiv) and dimethylsulfoxide (1 mL) were mixed in a microwave tube and capped. The microwave tube was reacted in a microwave reactor (Personel Chemistry, Emrys Optimizer) at 70° C. for 10 minutes. The solvent was removed by rotary evaporation and the crude product purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20) to return the title compound as a white solid (27.2 mg, 0.07 mmol, 34% yield). Analytical data presented in Table 1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071581B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-46c8a1a2cc694283bc5cc4314559f1d9 |
| Source note | uspto-grants-2011_12 |