Reaktion #531818
ord-cc9345925d1249abb23c8341bead0fc5
Reaktionsgleichung
Edukte
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1TemperaturThe reaction mixture was heated
- 2Temperaturat reflux for 4.5 hours
- 3SonstigeThin layer chromatography on silica gel confirmed completion of the reaction
- 4Filtrationfiltered through Celite®
- 5Waschenby washing three times with 10% aqueous sodium bicarbonate solution
- 6ExtraktionThe organic extract
- 7Trocknenwas dried (MgSO4)
- 8Einengenconcentrated under reduced pressure
- 9Sonstigethe residual solid was purified by chromatography on silica gel
Vorschrift
To a solution of 1-(3-chloro-2-pyridinyl)-N-[4-iodo-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (i.e. the diamide product of Step A) (410 mg, 0.72 mmol) in tetrahydrofuran (8 mL) was added copper(I) iodide (24 mg, 0.126 mmol), tetrakis(triphenyphosphine)palladium(0) (70 mg, 0.060 mmol) and copper(I) cyanide (640 mg, 7.2 mmol) sequentially at room temperature. The reaction mixture was heated at reflux for 4.5 hours. Thin layer chromatography on silica gel confirmed completion of the reaction. The reaction mixture was then diluted with ethyl acetate (20 mL) and filtered through Celite®, followed by washing three times with 10% aqueous sodium bicarbonate solution and once with brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure and the residual solid was purified by chromatography on silica gel to afford 114 mg of the title compound, a compound of the present invention, as a white solid, melting at 214-216° C.