Diglyme → 2-(2,2-Diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 42587노트

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HRID 42587 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:33][CH:34]([O:38][CH2:39][CH3:40])[O:35][CH2:36][CH3:37].COCCOCCOC>O.CCOC(C)=O>[CH2:36]([O:35][CH:34]([O:38][CH2:39][CH3:40])[CH2:33][N:28]1[CH:29]=[C:9]2[C:10]([N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:27]1)[CH3:37].[CH2:36]([O:35][CH:34]([O:38][CH2:39][CH3:40])[CH2:33][N:27]1[C:10]2=[N:11][C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]2[CH:29]=[N:28]1)[CH3:37]

참가 물질

7

반응물 4

HCID 8150DiglymeHCID 14797Potassium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

생성물 2

HCID 684434952-(2,2-Diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine수율 53%HCID 68445205HCID 68445205, 화합물수율 24%

시약·촉매·용매 1

HCID 22728543Water ethylacetate용매

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온도
100 °C

실험 절차

In a volumetric flask 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.5 mmol, obtained in example 1), KOH (0.03 g, 0.5 mmol), 2-bromo-1,1-diethoxyethane (0.10 g, 0.5 mmol) and 1-methoxy-2-(2-methoxyethoxy)ethane (2 mL) were introduced under argon atmosphere. The mixture was heated to 100° C. and stirred at this temperature overnight. It was allowed to cool and a mixture of H2O-EtOAc was added. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were 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 139 mg of 2-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 53%) and 60 mg of 1-(2,2-diethoxyethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 24%).

후처리

  1. temperatureto cool
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic phases were 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-6e4b4d4581334e88b299705a8deef39f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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