Pyrazol-3-ylamine → 4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

HRID 42567

반응식

HRID 42567 반응식
[NH2:1][C:2]1[NH:3][N:4]=[CH:5][CH:6]=1.FC1C=CC(C(O[C:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=O)=CC=1>CCO.Cl.C(Cl)(Cl)Cl.CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:15]2[C:16]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)=[C:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[N:1]=[C:2]3[NH:3][N:4]=[CH:5][C:6]=23)=[CH:28][CH:27]=1

참가 물질

7

반응물 2

HCID 74561Pyrazol-3-ylamineHCID 684458621-(4-Fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoate

생성물 1

HCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine수율 23%

시약·촉매·용매 4

HCID 313Hydrochloric Acid촉매HCID 702Ethanol용매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

To a solution of 3-amino-2H-pyrazole (60 mg, 71.8 mmol) in EtOH (2 mL) and 1 drop of 37% HCl, 1-(4-fluorophenyl)-2-(4-pyridyl)vinyl 4-fluorobenzoate (0.22 g, 65.0 mmol, obtained in reference example 4) was added under argon atmosphere. This was heated to reflux for 3 days. The mixture was diluted with CHCl3 and MeOH. It was washed with saturated NaHCO3. The aqueous phase was extracted with CHCl3 (×2). The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 58 mg of the desired product in a solid white form (yield: 23%).

후처리

  1. temperatureThis was heated
  2. temperatureto reflux for 3 days
  3. washIt was washed with saturated NaHCO3
  4. extractionThe aqueous phase was extracted with CHCl3 (×2)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customwas purified by chromatography on silica gel
  9. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-4cbd8a706b52416aa85386b5b15613c0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

연결된 노트

불러오는 중…