Water → 4-Isobutoxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498020Notes

Reaction equation

HRID 498020 reaction equation
[CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:3]=1.[H-].[Na+].[CH2:24](I)[CH:25]([CH3:27])[CH3:26].O>CN(C)C=O>[CH2:24]([O:15][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]2[N:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:3]=[C:2]([CH3:1])[C:14]=12)[CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 1358480443-Methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

Product 1

HCID 223203944-Isobutoxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one (1.93 g, 7.0 mmol) in N,N-dimethylformamide (30 mL), sodium hydride (oiliness, content 60%, 0.42 g, 10.5 mmol) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, isobutyl iodide (2.0 mL, 17.4 mmol) was added to the mixture, and the mixture was stirred at room temperature for 16 hours, and heated under reflux at 70° C. for 8 hours. The reaction solution was allowed to cool and iced water was added to the mixture, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate:chloroform=3:1:1) to give the title compound (0.54 g, 23% yield).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. temperatureheated
  3. temperatureunder reflux at 70° C. for 8 hours
  4. temperatureto cool
  5. extractionthe organic matter was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by basic silica gel column chromatography (hexane:ethyl acetate:chloroform=3:1:1)

Sources & evidence

ORD record
ord-c277768b3c9643ac9516aa8a785cdddd
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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