Reacción #1583828

ord-885bb276bc714bda84a0ee56749b6ff4

Ecuación de reacción

COC(=O)NCc1cc(-c2cc[nH]n2)ccc1Cl
methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate
FC(F)(F)Oc1cccc(CBr)c1
1-(bromomethyl)-3-(trifluoromethoxy)benzene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COC(=O)NCc1cc(-c2ccn(Cc3cccc(OC(F)(F)F)c3)n2)ccc1Cl
title compound
COC(=O)NCc1cc(-c2ccn(Cc3cccc(OC(F)(F)F)c3)n2)ccc1Cl
methyl N-[[2-chloro-5-[1-[[3-(trifluoromethoxy)phenyl]methyl]-1H-pyrazol-3-yl]phenyl]methyl]carbamate

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated under reduced pressure
  2. 2
    OtroThe resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant)

Procedimiento

A mixture of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Step B, Example 4) (0.2 g, 0.75 mmol), 1-(bromomethyl)-3-(trifluoromethoxy)benzene (0.765 g, 3.0 mmol) and potassium carbonate (−325 mesh, 0.829 g, 6.0 mmol) in N,N-dimethylformamide (4 mL) was heated at 100° C. overnight and then concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (0.178 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09198433B2uspto-grants-2015_12