HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 500576Generated: October 25, 2026
N-methyl-2-pyrrolidone → 5-Cyano-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester
https://huagongshe.com/reaction/500576
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate | HCID 59519391 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 5-Cyano-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester | HCID 86598642 | — |
Reaction Steps
A mixture of 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester (1.00 equiv.), dppf (0.02 equiv.), Pd2dba3 (0.01 equiv.), and Zn(CN)2 (0.60 equiv.) in NMP is stirred at 120° C. in a sealed tube. After stirring for 20 hours, the reaction mixture is cooled to room temperature and quenched with a 4:1:4 (volume) mixture solution of saturated aqueous NH4Cl-conc NH4O-water. The mixture is extracted with EtOAc. The organic layer is washed with saturated aqueous NH4Cl/concentrated NH4OH/water, and brine. The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is purified by flash column chromatography to afford the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07772234B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-a7036860263343c48869817e57257f9a |
|---|
| Source note | uspto-grants-2010_08 |
|---|
