4-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline → 4-(2-Fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline

HRID 7493

Reaktionsgleichung

Reaktionsgleichung von HRID 7493
C([O:8][C:9]1[C:10]([CH3:34])=[CH:11][C:12]([F:33])=[C:13]([CH:32]=1)[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[N:17][CH:16]=1)C1C=CC=CC=1>CO.CN(C=O)C.[Pd]>[F:33][C:12]1[CH:11]=[C:10]([CH3:34])[C:9]([OH:8])=[CH:32][C:13]=1[O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[N:17][CH:16]=1

Komponenten

5

Edukt 1

HCID 219910634-(5-Benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline

Produkt 1

HCID 219910644-(2-Fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnolineAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline (242 mg 0.5 mmol) in a mixture of methanol (9 ml) and DMF (10.5 ml) containing 10% palladium-on-charcoal catalyst (100 mg) was stirred under hydrogen at 5 atmospheres pressure for 9 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was washed with methanol and ether and dried under vacuum to give 4-(2-fluoro-5-hydroxy-4-methylphenoxy)-6-methoxy-7-(2-methoxyethoxy)cinnoline as a white solid (87 mg, 44%).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. washThe residue was washed with methanol and ether
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3806cfe94ac247309d3610fb7b304642
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087602B2

Verknüpfte Notizen

Wird geladen…