Reacción #41554

Ecuación de reacción

ethanol

1-(2-(5-amino-2-(4-methanesulfonyl-phenoxy)-4-nitro-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone

pyridine-2-carboxaldehyde

hydrogen

→

compound

2,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Disolventes

Water

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction liquid
2. 2
   OtroThe catalyst was removed through filtration through Celite
3. 3
   Otrothe solvent was evaporated away under reduced pressure
4. 4
   Otroto obtain a crude product
5. 5
   Otrothe reaction liquid
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   LavadoThe organic layer was washed with water and saturated saline
8. 8
   Secadodried with anhydrous sodium sulfate
9. 9
   OtroThe solvent was evaporated away under reduced pressure
10. 10
    Otrothe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1)

Procedimiento

100 mg of developed Raney nickel catalyst was added to an ethanol (10 ml) solution of 521 mg of 1-(2-(5-amino-2-(4-methanesulfonyl-phenoxy)-4-nitro-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone, and the reaction liquid was stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure to obtain a crude product. 226 mg of pyridine-2-carboxaldehyde was added to a methanol (10 ml) solution of 448 mg of the resulting crude product, and the reaction liquid was stirred overnight at 50° C. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1) to obtain the entitled compound as a pale yellow solid.

Fuente