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

HRID 989171Notes

Reaction equation

HRID 989171 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I:9])[CH:8]=1)[NH2:5].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22])[NH:17][CH2:16][CH2:15]2.[OH2:25].Cl[CH2:27]Cl>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:27]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([O:11][CH3:10])=[C:20]([C:21]([F:24])([F:22])[F:23])[CH:19]=3)[CH2:15][CH2:16]2)=[O:25])[CH:6]=[C:7]([I:9])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 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 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoro-5-iodoaniline (0.47 g, 1.98 mmol) and 1,1′-carbonyl imidazole (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 the title compound (0.38 g, 40%), m.p. 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

Sources & evidence

ORD record
ord-995d21a0a8da4ec2ad7b2d07f79c4377
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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