Reacción #8358

ord-5117de9338de4a369384dbd7fc1bb107

Ecuación de reacción

O=S(=O)(Cl)Cl
sulfuryl chloride
ClCCl
dichloromethane
Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1
7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline
ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21
title compound
ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21
7-Bromo-4-(4-chloro-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated in vacuo
  2. 2
    OtroThe residue is partitioned between chloroform and saturated sodium chloride
  3. 3
    SecadoThe organic layer is dried (sodium sulfate)
  4. 4
    Filtraciónfiltered
  5. 5
    Concentraciónconcentrated in vacuo
  6. 6
    Otrothe residue chromatographed on SiO2 (dichloromethane to 20% methanol in dichloromethane)

Procedimiento

A solution of 1 M sulfuryl chloride in dichloromethane (20 mL, 20 mmol) is added to a solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (2.2 g, 5.62 mmol) in dry pyridine (50 mL). The mixture is stirred for 18 h and concentrated in vacuo. The residue is partitioned between chloroform and saturated sodium chloride. The organic layer is dried (sodium sulfate), filtered, concentrated in vacuo, and the residue chromatographed on SiO2 (dichloromethane to 20% methanol in dichloromethane) to yield the title compound as a red solid, 1.8 g (75%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07087626B2uspto-grants-2006_08