Acetic Acid → N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamide

HRID 2201776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201776
CN(C)/[CH:3]=[CH:4]\[C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=1.C(O)(=O)C>CO.ClCCl.[Pd]>[NH:11]1[C:10]2=[CH:9][N:8]=[C:7]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=[C:5]2[CH:4]=[CH:3]1

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 86720622N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide

Produkt 1

HCID 18975304N-(1H-Pyrrolo[2,3-c]pyridin-5-yl)acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-{4-[(Z)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl}acetamide (0.7 g, 3 mmol, Step b) in methanol and dichloromethane (5:1, 120 mL), palladium on carbon (0.4 g) was added followed by addition of acetic acid (7 mL). The reaction mixture was then purged with hydrogen gas and stirred overnight at room temperature. The resulting mixture was filtered over celite bed, and the residue was washed with methanol (100 mL). The combined filtrate was concentrated under vacuum and purified by silica gel column chromatography using methanol in dichloromethane (2%) to afford N-(1H-pyrrolo[2,3-c]pyridin-5-yl)acetamide (0.35 g, 71%).

Aufarbeitung

  1. customThe reaction mixture was then purged with hydrogen gas
  2. filtrationThe resulting mixture was filtered over celite bed
  3. washthe residue was washed with methanol (100 mL)
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-26f574d25e514996baed44c8fd8b2da6
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09364466B2

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