Water → 6-Fluoro-3-(4-{[3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 573367노트

반응식

HRID 573367 반응식
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:21][O:22][CH2:23][CH2:24][N:25]1[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[N:27]=[C:26]1S(C)(=O)=O.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:26]4[N:25]([CH2:24][CH2:23][O:22][CH3:21])[C:29]5=[N:30][CH:31]=[CH:32][CH:33]=[C:28]5[N:27]=4)=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1364090944-(6-Fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

생성물 1

HCID 667280596-Fluoro-3-(4-{[3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine수율 44%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-(6-fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol (37 mg) in DMF (4 mL) was added NaH (60% in oil, 4.02 mg) at room temperature. The mixture was stirred at room temperature for 30 min, and then 3-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (52 mg) was added. The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The product was crystallized from EtOH/hexane to give the title compound (28.0 mg).

후처리

  1. customirradiation at 180° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  6. customThe product was crystallized from EtOH/hexane

출처 및 근거

ORD 기록
ord-bb6df8bde08f4748b6c734ef47395d13
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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