HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Bromo-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester → 1-Cyano-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Bromo-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester | HCID 89812977 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 1-Cyano-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester | HCID 89812911 | 73.4% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
A mixture of 1-bromo-7-(2,6-difluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester (156 mg) and CuCN (66 mg) in NMP was stirred at 150° C. for 1 h; then cooled, diluted with DCM, filtered, then washed with water, dil. NaCl solution, dried over sodium sulphate, filtered, concentrated, the residue was column purified to give the desired product (100 mg). LC MS ESI: 371 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409892B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-f8a6de4514164ca9a412bf71e89e58a9 |
| Source note | uspto-grants-2016_08 |