Reacción #674291

ord-21ff33de154f4f3c9b01e23b0c8d723c

Ecuación de reacción

CC(Oc1cccnc1N)c1c(Cl)ccc(F)c1Cl
3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine
O=C1CCC(=O)N1Br
NBS
CC(Oc1cc(Br)cnc1N)c1c(Cl)ccc(F)c1Cl
5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine
Rendimiento 82.5%

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe precipitate was removed by filtration
  2. 2
    ConcentraciónThe black filtrate was concentrated
  3. 3
    Otroto give a black residue which
  4. 4
    Otrowas purified by CombiFlash (80 g silica gel column, EtOAc/Hexane)

Procedimiento

To a solution of 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine (7.49 g, 24.87 mmol) in CH3CN/DCM (100/30 mL) was added NBS (4.43 g, 24.87 mmol) in portions at 0° C. The reaction solution was stirred at 0° C. for 10 min. The precipitate was removed by filtration. The black filtrate was concentrated to give a black residue which was purified by CombiFlash (80 g silica gel column, EtOAc/Hexane) to afford 5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (7.8 g, 82%) as a pale yellow solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09226923B2uspto-grants-2016_01