Reaction #62302

ord-865ce43855854fc9a49b8c44a516990f

Reaction equation

N#Cc1cc(F)c2c(c1)c(Br)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1
3-bromo-7-fluoro-1-trityl-1H-indazole-5-carbonitrile
C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
vinyltributyltin
→
C=Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2c(F)cc(C#N)cc12
title compound
C=Cc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2c(F)cc(C#N)cc12
7-Fluoro-1-trityl-3-vinyl-1H-indazole-5-carbonitrile

Reactants

N#Cc1cc(F)c2c(c1)c(Br)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1
3-bromo-7-fluoro-1-trityl-1H-indazole-5-carbonitrile
—
tetrakis(triphenylphosphilne)palladium(0)
C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
vinyltributyltin

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling to room temperature
  2. 2
    workup.ADDITION10 g of silica gel was added
  3. 3
    Otherthe solvent was evaporated
  4. 4
    Otherfollowed by purification by silica gel column chromatography

Procedure

Under nitrogen atmosphere, 3.32 g of 3-bromo-7-fluoro-1-trityl-1H-indazole-5-carbonitrile was dissolved in 100 mL of toluene, added with 398 mg of tetrakis(triphenylphosphilne)palladium(0) and 2.50 mL of vinyltributyltin, and stirred at 100° C. for 95 minutes. After cooling to room temperature, 10 g of silica gel was added, the solvent was evaporated, followed by purification by silica gel column chromatography, to afford 2.59 g of the title compound as white crystals.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07429609B2uspto-grants-2008_09