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

HRID 498018Notes

Reaction equation

HRID 498018 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+].I[CH2:25][CH3:26]>CN(C)C=O>[CH2:25]([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)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1358480443-Methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

Product 1

HCID 223203344-Ethoxy-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 34%

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 (2.76 g, 10 mmol) in N,N-dimethylformamide (30 mL) was added sodium hydride (oiliness, content 60%, 0.48 g, 12 mmol), and the mixture was stirred at room temperature for 1 hour. Subsequently, iodoethane (1.96 mL, 24.5 mmol) was added to the mixture and the mixture was stirred at room temperature further for 16 hours. Ice 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 (1.02 g, 34% yield).

Workup

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

Sources & evidence

ORD record
ord-c5154ec446114a499ad2fc47fda18035
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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