Isopropanol → 4-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573341Notes

Reaction equation

HRID 573341 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[CH2:25]([NH:27][NH2:28])[CH3:26].CC(O)C>O>[CH2:25]([N:27]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([F:24])[CH:21]=2)[C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[N:28]1)[CH3:26]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 29062EthylhydrazineHCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

Product 1

HCID 1363976944-(1-Ethyl-6-fluoro-1H-pyrazolo[4,3-b]pyridin-3-yl)phenolYield 69.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (400 mg), ethylhydrazine (369 mg) and 2-propanol (5 mL) was stirred at room temperature for 30 min, and at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in EtOH (40 mL) and 10% Pd—C (50% wet, 400 mg) was added. The mixture was stirred at room temperature for 1 h under H2 atmosphere, filtered and evaporated. The residue was suspended in AcOEt/IPE and collected by filtration to give the title compound (220 mg).

Workup

  1. waitat 90° C. for 12 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in EtOH (40 mL)
  6. addition10% Pd—C (50% wet, 400 mg) was added
  7. stirringThe mixture was stirred at room temperature for 1 h under H2 atmosphere
  8. filtrationfiltered
  9. customevaporated
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-213f231760d942f5ae48c884aa9b67fe
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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