Pyrrolidine → 5-methoxy-1H-pyrrolo(2,3-c)pyridine

HRID 1070743

Reaktionsgleichung

Reaktionsgleichung von HRID 1070743
[CH3:1][O:2][CH:3](OC)[N:4]([CH3:6])C.N1CCCC1.CO[C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([N+:23]([O-])=O)=CN=1>CN(C)C=O.[Pd]>[CH3:1][O:2][C:3]1[CH:22]=[C:20]2[CH:21]=[CH:16][NH:23][C:19]2=[CH:6][N:4]=1

Komponenten

6

Edukt 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 2431692-Methoxy-4-methyl-5-nitropyridine

Produkt 1

HCID 6410925-methoxy-1H-pyrrolo(2,3-c)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

10.76 g of N,N-dimethylformamide dimethyl acetal and 2.45 ml of pyrrolidine are added, in succession, to a solution of 5 g of the product obtained in Step 1 in 60 ml of dimethylformamide. The mixture obtained is first heated at 100° C. for 8 hours and then at 150° C. for 1 hour. Concentration is carried out under a vacuum of 10−1 mbar and the residue is taken up in 150 ml of tetrahydrofuran. The solution obtained is hydrogenated under a pressure of 10 bars for 4 hours in the presence of 10% Pd/C. After filtration and concentration, the residue is chromatographed over silica (eluant CH2Cl2/EtOH: 95/5) to yield the expected product.

Aufarbeitung

  1. customThe mixture obtained
  2. concentrationConcentration
  3. customThe solution obtained
  4. filtrationAfter filtration and concentration
  5. customthe residue is chromatographed over silica (eluant CH2Cl2/EtOH: 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-0af3fd6eda5341909e7973d76d8b9d8b
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903103B2

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