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

HRID 1603759노트

반응식

HRID 1603759 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de35233a49f0451b9bfb7ff00649797e
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990133

반응 노트

불러오는 중…