Water → 4-(1-Methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

HRID 573359Notes

Reaction equation

HRID 573359 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[NH:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI.O>CN(C=O)C>[CH3:24][N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866889913-[4-(Benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1364090934-(1-Methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenolYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-[4-(benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine (300 mg) and Cs2CO3 (649 mg) in DMF (4 mL) was added MeI (0.093 mL) at 0° C. The mixture was stirred at room temperature 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 (20 mL) and 10% Pd—C (50% wet, 200 mg) was added. The mixture was stirred for 1 h under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (160 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOH (20 mL)
  5. addition10% Pd—C (50% wet, 200 mg) was added
  6. stirringThe mixture was stirred for 1 h under H2 atmosphere
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-eab5cf088ed447c7b9b0b8468042a2e4
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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