Water → HCID 22320213, compound

HRID 498007Notes

Reaction equation

HRID 498007 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 under reflux at 100° C. for 30 minutes. The solution was cooled to room temperature, poured into water, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water and 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), 10% palladium-carbon (2 g, 50% hydrate) was added and the mixture was stirred at room temperature under hydrogen atmosphere for 1 hour. The solution was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure. The residue thus obtained 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. extractionthe organic matter was 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. filtrationThe solution was filtered
  8. customto remove the catalyst
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by basic silica gel column chromatography (ethyl acetate:methanol=95:5)

Sources & evidence

ORD record
ord-b65dee223f0b439898ff98484fd35ac1
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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