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

HRID 1603759ノート

反応式

HRID 1603759 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de35233a49f0451b9bfb7ff00649797e
出典データセット
uspto-grants-1999_11
特許番号
US05990133

反応ノート

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