Water → 2-Ethyl-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 2376728

Reaction equation

HRID 2376728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[OH-].[K+].O.[CH3:33][CH2:34]OC(C)=O>C1(C)C=CC=CC=1>[CH2:33]([N:28]1[CH:29]=[C:9]2[C:10]([N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:27]1)[CH3:34].[CH2:33]([N:27]1[C:10]2=[N:11][C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]2[CH:29]=[N:28]1)[CH3:34]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

Product 2

HCID 100702611-Ethyl-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 9%HCID 684447762-Ethyl-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.39 g, 0.8 mmol, obtained in example 1), KOH (0.05 g, 0.8 mmol) and crown ether 18-C-6 (0.01 g, 0.03 mmol) in toluene (3 mL) was heated to 100° C. for 2 h. A solution of lodoethane (0.18 g, 1.2 mmol) in toluene (1 mL) was added and stirred at 100° C. for 2 days. It was allowed to cool, water and EtOAc were added and the phases were separated. The aqueous phase was extracted with EtOAc. 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 0.20 g of 2-ethyl-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 61%) and 28 mg of 1-ethyl-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (yield: 9%).

Workup

  1. temperatureto cool
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product obtained
  7. customwas purified by chromatography on silica gel
  8. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-bbe4d5ea2e46412bb2843944d1c146fa
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Linked notes

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