Ammonium formate → 4-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol

HRID 916401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916401
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([F:30])=[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:31][CH3:32])C1C=CC=CC=1.C([O-])=O.[NH4+]>CN(C=O)C.[Pd].C(OCC)(=O)C>[F:30][C:21]1[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:31][CH3:32])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[C:24]([CH3:29])[NH:25]2

Komponenten

6

Edukt 2

HCID 2723923Ammonium formateHCID 101512047-(Benzyloxy)-4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazoline

Produkt 1

HCID 1355308324-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 7-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (8.2 g, 19.1 mmol), ammonium formate (12 g, 190 mmol) in DMF (50 ml) containing 10% palladium on carbon (2 g) was stirred at ambient temperature for 1.5 hours. The mixture was diluted with ethyl acetate and filtered over diatomaceous earth A solid precipitated out of the filtrate. The solid was filtered off. The filtrate was washed with aqueous sodium hydrogen carbonate, followed by brine and dried over magnesium sulphate. The volatiles were removed under vacuum. The residual solid was combined with the solid previously isolated from the filtrate and was then triturated with acetonitrile under cooling. The precipitate was filtered, washed with acetonitrile followed by diethyl ether and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (6.48 g, quant.).

Aufarbeitung

  1. filtrationfiltered over diatomaceous earth A solid
  2. customprecipitated out of the filtrate
  3. filtrationThe solid was filtered off
  4. washThe filtrate was washed with aqueous sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulphate
  6. customThe volatiles were removed under vacuum
  7. custompreviously isolated from the filtrate
  8. customwas then triturated with acetonitrile
  9. temperatureunder cooling
  10. filtrationThe precipitate was filtered
  11. washwashed with acetonitrile
  12. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-289456bb6a3f4541a75a458c7bda6fe1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268230B2

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