HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 68596094, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 2734385 | — |
| Reactant | methyl N-(5-bromo-2-chloro-anilino)carbamate | HCID 68595216 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 68596094 | HCID 68596094 | — |
Reaction Steps
A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate (i.e. the product of Step B) (1.27 g, 4.5 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesium carbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL) and methanol (60 mL) was heated at refluxed for 24 h. After cooling, the reaction mixture was taken up in diethyl ether and washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 25% ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g), which was a mixture of starting material and the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822521B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-94fffa4b5ac74c7081cae23989f1ab60 |
| Source note | uspto-grants-2014_09 |