Ammonium formate → 4-(2,3-Dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline

HRID 454092

Reaktionsgleichung

Reaktionsgleichung von HRID 454092
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])=[C:23]4[CH3:30])=[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]>[CH3:29][C:24]1[NH:25][C:26]2[C:22]([C:23]=1[CH3:30])=[CH:21][C:20]([O:19][C:13]1[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]=1)=[CH:28][CH:27]=2

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 220308297-Benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline

Produkt 1

HCID 1357631184-(2,3-Dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazolineAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 7-benzyloxy-4-(2,3-dimethylindol-5-yloxy)-6-methoxyquinazoline (2 g, 4.7 mmol) in DMF (120 ml) containing ammonium formate (11 gr, 174 mmol) and 10% palladium on charcoal (200 mg) was stirred for 2.5 hours at ambient temperature. The mixture was filtered, and the filtrate was evaporated under vacuum. The residue was triturated with ether and the solid was filtered, washed with water followed by ether and dried under vacuum at 50° C. to give 4-(2,3-dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (1.1 g, 69%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was triturated with ether
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customdried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-7218090d733b4b65ac2cc4aa660ad0b1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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