Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Chloro-5-(trifluoromethyl)pyridine | HCID 92342 | — |
| Reactant | 4-Benzyloxy-phenylboronic acid | HCID 2734314 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67153507 | HCID 67153507 | — |
Reaction Steps
A mixture of 2-chloro-5-trifluoromethylpyridine (1.81 g, 10 mmol), 4-benzyloxyphenyl boronic acid (2.74 g, 12 mmol) and CsF (5.32 g, 35 mmol) in dioxane (40 mL) is degaseed and filled with nitrogen. PdCl2(dppf) (200 mg) is added under nitrogen, the reaction mixture is heated at 105° C. overnight. The mixture is cooled to room temperature, diluted with ethyl acetate (100 mL), filtered through a pad of Celite. The filtrate is concentrated and the residue is purified by column chromatography on silica gel giving the title compound (2.55 g, 77.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07816557B2 |
|---|
| Source dataset | uspto-grants-2010_10 |
|---|
| ORD ID | ord-10ab31dcbe014fd1862fd0365e1d7a88 |
|---|
| Source note | uspto-grants-2010_10 |
|---|
