1-(6-Fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine → 1-(6-Fluoro-2-pyridyl)-6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57814Notes

Reaction equation

HRID 57814 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([C:23]([CH3:25])=[CH2:24])[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 867070211-(6-Fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 867070221-(6-Fluoro-2-pyridyl)-6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridineYield 82%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of the aforesaid 1-(6-fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine in Ethanol (50 mL) in a 250 mL round bottom flask was added Pearlman's catalyst (0.3523 mmol; 247.4 mg). The flask was vacuumed and connected with a balloon of Hydrogen. The mixture was stirred at room temperature for 16 hours. The mixture was filtered through Celite. The filtrate was concentrated. The residue was purified on silica eluted with 0 to 5% MeOH in DCM to afford 1-(6-fluoropyridin-2-yl)-6-(5-isopropylpyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine (479.2 mg, 82%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified on silica
  4. washeluted with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-a15fc0a7722741e3ba6e98b9d17813a8
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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