5-Methoxy-6-(trifluoromethyl)indoline → 1-(4-Chloro-3-(pyrid-3-yl)phenylcarbamoyl)-5-methoxy-6-trifluoromethylindoline

HRID 1603789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603789
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][C:34]=1[C:35]([F:38])([F:37])[F:36])[NH:31][CH2:30][CH2:29]2>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:31]2[C:32]3[C:28](=[CH:27][C:26]([O:25][CH3:24])=[C:34]([C:35]([F:37])([F:38])[F:36])[CH:33]=3)[CH2:29][CH2:30]2)=[O:17])=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005115Phenyl N-(4-Chloro-3-(pyrid-3-yl)phenyl)carbamate

Produkt 1

HCID 105995451-(4-Chloro-3-(pyrid-3-yl)phenylcarbamoyl)-5-methoxy-6-trifluoromethylindolineAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Phenyl N-(4-Chloro-3-(pyrid-3-yl)phenyl)carbamate (D67) (0.12 g, 0.00037 mole) in dry dimethylformamide (6 ml) was treated under argon, with 5-methoxy-6-trifluoromethylindoline (D11) (0.08 g, 0.00037 mole) and heated to 120° C. for 2 hours. After cooling to ambient temperature, the solvent was removed in vacuo. The residue was partitioned between 1N aqueous sodium hydroxide solution and dichloromethane. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was triturated in diethyl ether, filtered and dried in vacuo at 60° C. to afford the title compound (0.06 g, 36%) as a grey-green solid (mp 210-213° C.)

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between 1N aqueous sodium hydroxide solution and dichloromethane
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue was triturated in diethyl ether
  7. filtrationfiltered
  8. customdried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-ba2a8ce712c0449e8a8198279c3cfe65
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990133

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