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

HRID 573329노트

반응식

HRID 573329 반응식
[CH3:1][CH:2]([N:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[N:17][CH:18]=2)=[N:5]1)[CH3:3].[H-].[Na+].[CH3:22][N:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[N:25]=[C:24]1S(C)(=O)=O.O>CN(C=O)C>[CH3:3][CH:2]([N:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[CH:18]=[N:17][C:16]([O:19][C:24]3[N:23]([CH3:22])[C:27]4=[N:28][CH:29]=[CH:30][CH:31]=[C:26]4[N:25]=3)=[CH:15][CH:14]=2)=[N:5]1)[CH3:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 178456626HCID 178456626, 화합물

생성물 1

HCID 866889851-(1-Methylethyl)-3-{6-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]pyridin-3-yl}-1H-pyrazolo[4,3-b]pyridine수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 5-[1-(1-Methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]pyridin-2-ol (76 mg) in DMF (4 mL) was added NaH (60% in oil, 12.6 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (76 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 silica gel column chromatography (AcOEt/hexane). The product was crystallized from AcOEt/hexane to give the title compound (23.0 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 silica gel column chromatography (AcOEt/hexane)
  6. customThe product was crystallized from AcOEt/hexane

출처 및 근거

ORD 기록
ord-636e72f6eae044b689050f737a8d29a7
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

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