Reaktion #41554

Reaktionsgleichung

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

Lösungsmittel

Water

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle