Water → 4-[(4-fluoro-1H-indol-5-yl)oxy]-6-hydroxy-7-methoxyquinazoline

HRID 916413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916413
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2[O:21][C:22]1[C:23]([F:31])=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[CH:25]2)C1C=CC=CC=1.C([O-])=O.[NH4+].O>[Pd].CN(C=O)C>[F:31][C:23]1[C:22]([O:21][C:12]2[C:11]3[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=3)[N:15]=[CH:14][N:13]=2)=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[CH:26][NH:27]2

Komponenten

6

Edukt 3

HCID 962WaterHCID 2723923Ammonium formateHCID 589602306-Benzyloxy-4-(4-fluoroindol-5-yloxy)-7-methoxyquinazoline

Produkt 1

HCID 589602194-[(4-fluoro-1H-indol-5-yl)oxy]-6-hydroxy-7-methoxyquinazolineAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Benzyloxy-4-(4-fluoroindol-5-yloxy)-7-methoxyquinazoline (0.75 g, 1.8 mmol), ammonium formate (1.14 g, 18 mmol) and 10% palladium on carbon (115 mg) in DMF (8 ml) containing water (1.5 ml) was stirred at ambient temperature for 2.5 hours. The mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was triturated under diethyl ether, filtered, washed with water, followed by diethyl ether and dried overnight over P2O5 to give 4-(4-fluoroindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline (0.471 g, 80%).

Aufarbeitung

  1. filtrationThe mixture was filtered over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residue was triturated under diethyl ether
  4. filtrationfiltered
  5. washwashed with water
  6. dry with materialdried overnight over P2O5

Quellen und Nachweise

ORD-Eintrag
ord-0354d93ae944420fa9bb57b4187ad920
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268230B2

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