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

HRID 1603759Notes

Reaction equation

HRID 1603759 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-de35233a49f0451b9bfb7ff00649797e
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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