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

HRID 573355
Notes
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Reaction equation

HRID 573355 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH:11]([CH3:13])[CH3:12])[N:9]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:23][N:24]1[C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[N:26]=[C:25]1S(C)(=O)=O.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH:11]([CH3:13])[CH3:12])[N:9]=[C:8]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:25]4[N:24]([CH3:23])[C:28]5=[N:29][CH:30]=[CH:31][CH:32]=[C:27]5[N:26]=4)=[CH:18][CH:19]=3)[C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1364090924-[6-Fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenol

Product 1

HCID 866889946-Fluoro-1-(1-methylethyl)-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridineYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-[6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridin-3-yl]phenol (76 mg) in DMF (4 mL) was added NaH (60% in oil, 11.2 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 (59.2 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 AcOEt/hexane to give the title compound (60.0 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 AcOEt/hexane

Sources & evidence

ORD record
ord-d47baa43603342b996cc329c0455c85f
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes