Trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane → 2-[[6-(5-Ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl-trimethyl-silane

HRID 57827Notes

Reaction equation

HRID 57827 reaction equation
[CH3:1][Si:2]([CH3:25])([CH3:24])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[CH:14]=[C:13]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH:22]=[CH2:23])[CH:21]=3)[N:12]=[CH:11][C:10]=2[CH:9]=[N:8]1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:22]([C:20]1[CH:21]=[C:16]([C:13]2[N:12]=[CH:11][C:10]3[CH:9]=[N:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:24])([CH3:1])[CH3:25])[C:15]=3[CH:14]=2)[CH:17]=[N:18][CH:19]=1)[CH3:23]

Participants

5

Reactant 2

HCID 86707031Trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silaneHCID 178418361HCID 178418361, compound

Product 1

HCID 867070332-[[6-(5-Ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl-trimethyl-silaneYield 27%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane (543.4 mg) in Ethanol (50 mL) in a 250 mL round bottom flask was added Pearlman's catalyst (0.1850 mmol; 129.9 mg). The flask was vacuumed and connected with a balloon of Hydrogen. The mixture was stirred at room temperature overnight. 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 2-[[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl-trimethyl-silane (87 mg, 27%).

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-04d999c29e2548828d0a0afd5bf4afdd
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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