HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-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 | 5-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide | HCID 86728469 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-chloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide | HCID 78323426 | 30.3% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
Cs2CO3 (879.9 mg, 2.7 mmol) was added to a solution of 2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-5-chlorobenzamide (72.0 mg, 0.27 mmol) and 4-fluoro-3-methoxyphenol (307.7 μl, 2.7 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 5-chloro-2-(4-fluoro-2-methoxyphenoxy)-N-(2-oxo-1,2-dihydropyridin-4-yl)benzamide (7a) (31.8 mg, 30%). ESI-MS m/z calc. 388.06, found 389.10 (M+1)+; Retention time: 1.52 minutes (3 minutes run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09163042B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-72299082931d4e169fa95e395cac6746 |
| Source note | uspto-grants-2015_10 |