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

HRID 57826Notes

Reaction equation

HRID 57826 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:33]=[CH2:34])[CH:32]=2)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH3:16][Si:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][O:12][CH2:11][N:10]1[C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[N:29][CH:30]=[C:31]([CH:33]=[CH2:34])[CH:32]=3)[N:7]=[CH:6][C:5]=2[CH:8]=[N:9]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 867070302-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silaneHCID 867070323-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-vinylpyridine

Product 1

HCID 86707031Trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silaneYield 143.5%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-[(6-chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane (1.074 mmol; 304.8 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-vinyl-pyridine (1.611 mmol; 372.3 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.1074 mmol; 89.5 mg), potassium acetate (1.611 mmol; 1.6 mL) and sodium carbonate (1.611 mmol; 1.6 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 5 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford trimethyl-[2-[[6-(5-vinyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]methoxy]ethyl]silane (543.4 mg, 86%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layer was concentrated
  5. customThe residue was purified on silica
  6. washeluted with 0 to 6% MeOH in DCM

Sources & evidence

ORD record
ord-590b3cf8006645918e3321c7a7a891b4
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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