반응 #41554

반응 방정식

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

용매

Water

methanol

반응 조건

후처리

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

실험 절차

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.

출처