HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 8-fluoro-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | 7-Bromo-8-fluoro-2-methylquinoline | HCID 70983354 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 8-fluoro-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)quinoline | HCID 70983984 | 87.6% |
Reaction Steps
A solution of 7-bromo-8-fluoro-2-methylquinoline (0.15 g, 0.63 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.26 g, 1.25 mmol), PdCl2(dppf)*dcm (0.051 g, 0.063 mmol), CsF (0.247 g, 1.62 mmol) and triethylamine (0.13 mL, 0.94 mmol) in IPA (3 mL) was heated at 100° C. in a sealed tube for 6 hours. After cooling to ambient temperature, water (10 mL) and ethyl acetate (20 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate) to give 8-fluoro-2-methyl-7-(1-methyl-1H-pyrazol-4-yl)quinoline (0.132 g, 87.6%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889704B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-3e951482ec4c49ef8f38cb69c7060fda |
| Source note | uspto-grants-2014_11 |