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

HRID 13276

Reaktionsgleichung

Reaktionsgleichung von HRID 13276
C(O)C.[NH2:4][C:5]1[C:6]([N+:33]([O-])=O)=[CH:7][C:8]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH:10]=1.[H][H].[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH:44]=O>[Ni].O.CO>[F:18][C:17]([F:20])([F:19])[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[C:9]1[C:8]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:7][C:6]2[N:33]=[C:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][N:38]=3)[NH:4][C:5]=2[CH:10]=1)=[O:21]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 142732-PyridinecarboxaldehydeHCID 231451471-(2-(5-Amino-2-(4-methanesulfonyl-phenoxy)-4-nitro-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 231457212,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c8231d564b8f4c74832616ebad262bfa
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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