4-Hydroxybenzaldehyde → 4-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]phenol

HRID 42586

반응식

HRID 42586 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[NH:19][N:20]=[CH:21][CH:22]=1.[OH:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.Cl.C([O-])(O)=O.[Na+]>COCCO.C(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:18]3[NH:19][N:20]=[CH:21][C:22]3=[C:28]([C:27]3[CH:30]=[CH:31][C:24]([OH:23])=[CH:25][CH:26]=3)[C:9]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 74561Pyrazol-3-ylamineHCID 516892Sodium BicarbonateHCID 103308811-(4-Fluorophenyl)-2-(pyridin-4-yl)ethan-1-one

생성물 1

HCID 1363678394-[6-(4-Fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]phenol수율 41.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매HCID 80192-Methoxyethanol용매2회

실험 절차

To a solution of 1-(4-fluorophenyl)-2-(4-pyridyl)ethanone (0.30 g, 1.4 mmol, obtained in reference example 1) in 2-methoxyethanol (2 mL), 3-amino-2H-pyrazole (0.13 g, 1.5 mmol), 4-hydroxybenzaldehyde (0.17 g, 1.4 mmol), 2-methoxyethanol (2 mL) and 37% HCl (0.04 g, 0.4 mmol) were added under argon atmosphere. The mixture was heated to reflux overnight. It was allowed to cool and concentrated. The solid obtained was dissolved in CHCl3 and some drops of MeOH. Saturated NaHCO3 was added and the aqueous phase was extracted 3 times with CHCl3. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.22 g of the desired compound (yield: 41%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureto cool
  4. concentrationconcentrated
  5. customThe solid obtained
  6. extractionthe aqueous phase was extracted 3 times with CHCl3
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe crude product was purified by chromatography on silica gel
  10. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-ca35d469f42b472ba26356e3dd442510
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

연결된 노트

불러오는 중…