Water → 1-(3-Fluoro-5-iodophenylcarbamoyl)-5-methoxy-6-trifluoromethylindoline

HRID 1603759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603759
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I:9])[CH:8]=1)[NH2:5].[C:10]([N:17]1[CH:21]=[CH:20]N=[CH:18]1)(N1C=CN=C1)=[O:11].[CH3:22][O:23][C:24]1[CH:25]=[C:26]2C(=[CH:31][C:32]=1[C:33]([F:36])([F:35])[F:34])NCC2.O>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]([N:17]2[C:18]3[C:26](=[CH:25][C:24]([O:23][CH3:22])=[C:32]([C:33]([F:35])([F:36])[F:34])[CH:31]=3)[CH2:20][CH2:21]2)=[O:11])[CH:6]=[C:7]([I:9])[CH:8]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 27589863-Fluoro-5-iodoanilineHCID 112067135-Methoxy-6-(trifluoromethyl)indoline

Produkt 1

HCID 180051431-(3-Fluoro-5-iodophenylcarbamoyl)-5-methoxy-6-trifluoromethylindolineAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-fluoro-5-iodoaniline (0.47 g, 1.98 mmol) and 1,1'-carbonyl diimidazole (0.33 g, 2 mmol) in dichloromethane (40 ml) was stirred at room temperature for 1 h, then evaporated to dryness. To the residue was added dimethylformamide (DMF,10 ml) and a solution of 5-methoxy-6-trifluoromethylindoline (D11, 0.44 g, 2 mmol) in DMF (5 ml). The mixture was heated at 80° C. overnight, then cooled and poured into water. The precipitate was filtered off, washed with water and dried. The crude product was chromatographed on silica gel and eluted with dichloromethane. Eluted product was recrystallised from dichloromethane to give tie title compound (0.38 g, 40%), Mp. 221-4° C.

Aufarbeitung

  1. customevaporated to dryness
  2. additionTo the residue was added dimethylformamide (DMF,10 ml)
  3. temperatureThe mixture was heated at 80° C. overnight
  4. temperaturecooled
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customThe crude product was chromatographed on silica gel
  9. washeluted with dichloromethane
  10. customEluted product was recrystallised from dichloromethane
  11. customto give

Quellen und Nachweise

ORD-Eintrag
ord-de35233a49f0451b9bfb7ff00649797e
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990133

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