HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-(Benzyloxy)-6-(6-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | 5-Bromo-2-methylpyridine | HCID 1201020 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | 5-(Benzyloxy)-6-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole | HCID 66767066 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-(Benzyloxy)-6-(6-methylpyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole | HCID 66767124 | 46.2% |
Reaction Steps
To a solution of 5-(benzyloxy)-6-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (4 g, 10.3 mmol) in 1,4-dioxane (25 mL) is added bis(pinacolato)diboron (3 g, 11.8 mmol), dppf (0.3 g, 541 μmol), PdCl2(dppf) (0.42 g, 514 μmol) and KOAc (2 g, 20.4 mmol) under N2. After the reaction mixture is stirred at reflux for 5 hours, 5-bromo-2-methylpyridine (2.1 g, 12.2 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.6 g, 519 μmol) and Cs2CO3 (4 g, 12.3 mmol) are added and the mixture is stirred at reflux overnight. The reaction mixture is cooled and filtered, the filtrate is concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (2:1) to give the product (1.9 g, 46.0% yield). MS (m/z): 400.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030302B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-3b136d0de8584be19934fae2556c9d03 |
| Source note | uspto-grants-2011_10 |