Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(Dimethylamino)benzeneboronic acid | HCID 2762527 | — |
| Reactant | 2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide | HCID 67110887 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67239540 | HCID 67239540 | 16.6% |
Reaction Steps
In a 5 ml glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol), 3-dimethylaminophenyl boronic acid (60 mg, 0.30 mmol), Cs2CO3 (129 mg, 0.40 mmol), Pd(PPh3)2Cl2(7 mg, 0.01 mmol), dimethoxyethane (0.8 mL), ethanol (0.2 mL), and a magnetic stir bar. The mixture was stirred at 140° C. for 20 minutes under microwave irradiation, acidified with 3N HCl, and extracted twice with EtOAc. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was triturated with ether to give title compound (10 mg, 16%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08691855B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-59c23e7611524050ad441f876a4d4e19 |
|---|
| Source note | uspto-grants-2014_04 |
|---|