Potassium Carbonate → 7-Benzyloxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 454086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454086
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([CH3:30])=[CH:24]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][C:25]([CH3:30])=[CH:24]4)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 833362-methyl-1H-indol-5-olHCID 220309237-(Benzyloxy)-4-chloroquinazoline

Produkt 1

HCID 220307817-Benzyloxy-4-(2-methylindol-5-yloxy)quinazolineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 7-benzyloxy-4-chloroquinazoline (2 g, 7.4 mmol), 5-hydroxy-2-methylindole (1.3 g, 8.9 mmol), (prepared as described for the starting material in Example 48), in DMF (20 ml) containing potassium carbonate (1.53 g, 11.1 mmol) was stirred at 80° C. for 3 hours. After cooling, the mixture was poured in portions into ice/water. The precipitate was filtered and washed with water and dried under vacuum. The solid was dissolved in methylene chloride and was purified by column chromatography eluting with ethyl acetate and methylene chloride (1/1) to give 7-benzyloxy-4-(2-methylindol-5-yloxy)quinazoline (2.28 g, 81%).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in methylene chloride
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate and methylene chloride (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-c52c142e03e547ba86b371fdd85500f7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492560B2

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