Dimethylformamide → 3,4-Dimethyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498039Notes

Reaction equation

HRID 498039 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH3:9].[CH3:11][C:12]1[CH:16]=[C:15]([NH2:17])[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20]C=2)[N:13]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+].C[N:36](C)C=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH3:11][C:12]1[C:16]2[C:15](=[N:17][C:2]3[C:3]([C:8]=2[CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:36]=2)[N:13]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 708015-Amino-3-methyl-1-phenylpyrazoleHCID 750602'-BromoacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 223202513,4-Dimethyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 15%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

A solution of o-bromoacetophenone (1.09 g, 5.5 mmol), 3-methyl-1-phenyl-1H-pyrazol-5-ylamine (0.87 g, 5.0 mmol), copper acetate (II) (91 mg, 0.5 mmol) and potassium carbonate (0.76 g, 5.5 mmol) in N,N-dimethylformamide (5 mL) was heated under reflux under an argon atmosphere for 1 hour. The solution was cooled to room temperature, and poured into water. The solution was made basic by the addition of a sodium bicarbonate solution, 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 silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (0.21 g, 15% yield).

Workup

  1. temperatureunder reflux under an argon atmosphere for 1 hour
  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 silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-db32a7bfb2db4baf9938c520bf5d9b58
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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