Potassium Carbonate → 1h-Indazole,5-(2-fluoro-4-nitrophenoxy)-

HRID 16399

反応式

HRID 16399 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1014381H-Indazol-5-olHCID 1230531,2-Difluoro-4-nitrobenzene

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-148ed9b344d04550bc6dd240a54fb706
出典データセット
uspto-grants-2010_06
特許番号
US07737153B2

関連ノート

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