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

HRID 16399

반응식

HRID 16399 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-148ed9b344d04550bc6dd240a54fb706
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737153B2

연결된 노트

불러오는 중…