Water → 2-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo(3,4-b]pyridine

HRID 42572Notes

Reaction equation

HRID 42572 reaction equation
[C:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:10]=[C:9]3[NH:25][N:26]=[CH:27][C:8]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].I[CH3:31].O>CC(C)=O>[CH3:31][N:26]1[CH:27]=[C:8]2[C:9]([N:10]=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:25]1.[CH3:31][N:25]1[C:9]2=[N:10][C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]2[CH:27]=[N:26]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 670148534,6-diphenyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

Product 2

HCID 670142511-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 38%HCID 684450762-Methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo(3,4-b]pyridineYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a suspension of 4,6-diphenyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.10 g, 0.3 mmol, obtained in example 2) in acetone (1 mL), KOH (21 mg, 0.4 mmol) was added under argon atmosphere. Then, a solution of iodomethane (47 mg, 0.3 mmol) in acetone (0.1 mL) was added and stirred overnight at room temperature. Water was added and extracted with CHCl3. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 47 mg of 2-methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 47%) and 38 mg of 1-methyl-4,6-diphenyl-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 38%).

Workup

  1. additionwas added under argon atmosphere
  2. extractionextracted with CHCl3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-db921462605e4900b5a92d0579ee40d8
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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