Ammonium formate → 7-Hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

HRID 454265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454265
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[C:23]4[CH3:29])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CN(C=O)C>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[C:23]4[CH3:29])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 220308717-Benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline

Produkt 1

HCID 1357631157-Hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazolineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 7-benzyloxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (7.76 g, 18.9 mmol), ammonium formate (17.82 g, 282 mmol) and 10% palladium on charcoal (800 mg) in DMF (350 ml) was stirred at ambient temperature for 1 hour. The catalyst was filtered off through celite and the cake washed with DMF. The solvent was removed in vacuo and the residue stirred with a saturated solution of sodium hydrogen carbonate for 2 hours. The suspension was then filtered, washed with water and dried to give 7-hydroxy-6-methoxy-4-(3-methylindol-5-yloxy)quinazoline (5.49 g, 91%).

Aufarbeitung

  1. filtrationThe catalyst was filtered off through celite
  2. washthe cake washed with DMF
  3. customThe solvent was removed in vacuo
  4. stirringthe residue stirred with a saturated solution of sodium hydrogen carbonate for 2 hours
  5. filtrationThe suspension was then filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aae70e5c129142d1a6d1a55d453d2249
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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