HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-chloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Fluoro-3-methoxyphenol | HCID 14118956 | — |
| Reactant | 4-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide | HCID 86728467 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-chloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide | HCID 78322164 | 28.4% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
Cs2CO3 (651.6 mg, 2.0 mmol) was added to a solution of 2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-4-chlorobenzamide (53.3 mg, 0.20 mmol) and 4-fluoro-3-methoxyphenol (284.3 mg, 2.0 mmol) in DMF (1 mL) and the reaction was stirred at 100° C. for 1 hour. The reaction was filtered and purified by reverse phase HPLC using a gradient of acetonitrile in water (10-99%) and HCl as a modifier to yield 4-chloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (16) (22.1 mg, 28%). ESI-MS m/z calc. 388.06. found 389.15 (M+1)+; Retention time: 1.53 minutes (3 minutes run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09051270B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-9682f34850894ca197ff61c2318e88c8 |
| Source note | uspto-grants-2015_06 |