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7-Benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline → 7-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline

HRID 1791590
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1791590
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][C:24]([CH3:29])=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31])C1C=CC=CC=1.[H][H]>C(Cl)Cl.CN(C=O)C.[Pd]>[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][C:24]([CH3:29])=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:30][CH3:31]
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Komponenten

6

Edukt 2

HCID 220308047-Benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazolineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1357631087-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazolineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 7-benzyloxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (0.2 g, 0.5 mmol), (prepared as described in Example 48), in a mixture of methylene chloride (5 ml) and DMF (2 ml) containing 10% palladium-on-charcoal (50 mg) was treated with hydrogen at 1.8 atmospheres pressure for 2 hours. The suspension was filtered and the catalyst was washed with methanol followed by methylene chloride. The volatiles were removed from the filtrate by evaporation. The residue was triturated with water. The resulting solid was washed with water and dried under vacuum over phosphorus pentoxide at 60° C. to give 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (140 mg, 89%).

Aufarbeitung

  1. filtrationThe suspension was filtered
  2. washthe catalyst was washed with methanol
  3. customThe volatiles were removed from the filtrate by evaporation
  4. customThe residue was triturated with water
  5. washThe resulting solid was washed with water
  6. dry with materialdried under vacuum over phosphorus pentoxide at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-89f73e14acf541e39c05386c43425075
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07074800B1

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