Water → HCID 22320213, compound

HRID 497961Notes

Reaction equation

HRID 497961 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[N-:22]=[N+]=[N-].[Na+].O>CN(C)C=O.[C].[Pd]>[CH3:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[NH2:22])=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320213HCID 22320213, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.44 g, 4.89 mmol) and sodium azide (0.35 g, 5.37 mmol) in N,N-dimethylformamide (10 mL) was heated and stirred at 100° C. for 30 minutes. The solution was cooled to room temperature and poured into water, and organic matter was extracted with chloroform. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a solution of the residue thus obtained in ethanol (70 mL) was added 10% palladium-carbon (2 g, 50% hydrate), and the mixture was stirred at room temperature for 1 hour under an hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5) to give the title compound (760 mg, 57% yield).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionwas extracted with chloroform
  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. customTo a solution of the residue thus obtained in ethanol (70 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hour under an hydrogen atmosphere
  8. customThe catalyst was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe resulting residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5)

Sources & evidence

ORD record
ord-443b09bcb2e949dd8d95577f66355591
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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