Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Butoxyphenylboronic acid | HCID 5084100 | — |
| Reactant | 2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide | HCID 67110887 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67237867 | HCID 67237867 | 39% |
Reaction Steps
In a glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (100 mg, 0.26 mmol), 2-butoxy phenyl boronic acid (61 mg, 0.32 mmol), 2N—Na2CO3 (0.5 mL), Pd(PPh3)4 (4.6 mg, 0.004 mmol), toluene (1.0 mL), ethanol (0.5 mL), and a magnetic stir bar. The mixture was stirred overnight at 110° C. and was diluted with EtOAc and water. The organic layer was washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (50 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08691855B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-ba29fa53eacd4603bb8b37d0f92579a6 |
|---|
| Source note | uspto-grants-2014_04 |
|---|