Potassium Carbonate → 3-Methyl-4-(propylsulfanyl)-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498022Notes

Reaction equation

HRID 498022 reaction equation
[CH3:1][C:2]1[C:14]2[C:13](=[S: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.I[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[S:15][CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 1358480753-Methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-thione

Product 1

HCID 223201473-Methyl-4-(propylsulfanyl)-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-thione (4.04 g, 13.8 mmol), 1-iodopropane (6.80 mL, 69.7 mmol) and potassium carbonate (3.79 g, 27.5 mmol) in N,N-dimethylformamide (25 mL) was stirred at room temperature for 8 hours. The reaction solvent was evaporated under reduced pressure. Water was added to the residue, and the organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was recrystallized from ethyl acetate/hexane to give the title compound (3.83 g, 83% yield).

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe organic matter was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-293d26914fa94ae0adabd5fc67558d62
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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