碳酸钾 → 1h-Indazole,5-(2-fluoro-4-nitrophenoxy)-

HRID 16399

反应方程式

HRID 16399 反应方程式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2

参与物

5

反应物 3

HCID 11430碳酸钾HCID 1014381H-吲唑-5-醇HCID 1230533,4-二氟硝基苯

产物 1

HCID 179793521h-Indazole,5-(2-fluoro-4-nitrophenoxy)-

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
40 °C

实验过程

5.00 g (37.3 mmol) of 5-hydroxyindazole are dissolved in 40 ml of anhydrous DMF. 5.93 g (37.3 mmol) of 3,4-difluoronitrobenzene and 5.15 g (37.3 mmol) of potassium carbonate are added, and the mixture is stirred at 40° C. overnight. For work-up, the mixture is filtered off with suction through kieselguhr, diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed 1× with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated using a rotary evaporator. The residue is chromatographed twice on silica gel using cyclohexane/ethyl acetate 3:1→1:1→1:2 and then purified by preparative HPLC.

后处理

  1. filtrationFor work-up, the mixture is filtered off with suction through kieselguhr
  2. additiondiluted with water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases are washed 1× with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. customThe residue is chromatographed twice on silica gel
  9. custompurified by preparative HPLC

来源与证据

ORD记录
ord-148ed9b344d04550bc6dd240a54fb706
来源数据集
uspto-grants-2010_06
专利号
US07737153B2

关联笔记

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