Reacción #62345

ord-ece1696588f2407289d727effe25fd70

Ecuación de reacción

N#Cc1cc2c(I)n[nH]c2cn1
3-iodo-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile
CCN(C(C)C)C(C)C
diisopropylethylamine
ClC(c1ccccc1)(c1ccccc1)c1ccccc1
trityl chloride
N#Cc1cc2c(I)nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c2cn1
title compound
Rendimiento 47.3%
N#Cc1cc2c(I)nn(C(c3ccccc3)(c3ccccc3)c3ccccc3)c2cn1
3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile
Rendimiento 47.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solution was evaporated
  2. 2
    workup.ADDITIONdiluted with ethyl acetate
  3. 3
    Lavadowashed successively with saturated ammonium chloride and saturated brine
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    OtroThe solvent was evaporated
  6. 6
    Otrothe crude product was purified
  7. 7
    Otroseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10)

Procedimiento

To a solution of 5.8 g of 3-iodo-1H-pyrazolo[3,4-c]pyridine-5-carbonitrile in 70 mL of dichloromethane were added 13.1 mL of diisopropylethylamine, 2.4 g of tetra-n-butylammonium iodide and 12.0 g of trityl chloride at room temperature, and stirred at this temperature for a day. The solution was evaporated, diluted with ethyl acetate, washed successively with saturated ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10), to afford 5.2 g of the title compound as colorless crystals.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07429609B2uspto-grants-2008_09