Cesium carbonate → 6-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline

HRID 916369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916369
[CH2:1]([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]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[C:31]([OH:32])=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[C:26]([CH3:33])[NH:27]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([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:32][C:31]1[C:23]([F:22])=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([CH3:33])=[CH:25]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 114265806-(Benzyloxy)-4-chloro-7-methoxyquinazoline

Produkt 1

HCID 666463136-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazolineAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-benzyloxy-4-chloro-7-methoxyquinazoline (0.39 g, 1.3 mmol), (EP1153920 production examples 28-30), 4-fluoro-5-hydroxy-2-methylindole (0.24 g, 1.43 mmol) and cesium carbonate (1.2 g, 4 mmol) in DMF (4 ml) was stirred at 95° C. for 45 minutes. After cooling, the mixture was filtered and the filtrate was evaporated under vacuum The residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and ethyl acetate to give 6-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline (0.213 g, 37%).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated under vacuum The residue
  4. customwas purified by column chromatography
  5. washeluting
  6. temperaturewith increasingly polar mixtures of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a2afab915d5d4541a23beb953c17a7f4
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268230B2

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