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

HRID 573363Notes

Reaction equation

HRID 573363 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:4]1)[CH3:2].[H-].[Na+].[CH3:22][O:23][CH2:24][CH2:25][N:26]1[C:30]2=[N:31][CH:32]=[CH:33][CH:34]=[C:29]2[N:28]=[C:27]1S(C)(=O)=O.O>CN(C=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:27]3[N:26]([CH2:25][CH2:24][O:23][CH3:22])[C:30]4=[N:31][CH:32]=[CH:33][CH:34]=[C:29]4[N:28]=3)=[CH:15][CH:14]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1363976944-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

Product 1

HCID 667281351-Ethyl-6-fluoro-3-(4-{[3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-1H-pyrazolo[4,3-b]pyridineYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(1-ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol (57.6 mg) in DMF (4 mL) was added NaH (60% in oil, 5.38 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 (38.0 mg).

Workup

  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

Sources & evidence

ORD record
ord-17ced0149a7c431ca8089b738512633e
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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