Reacción #60706

ord-7363ab9554e2406d92b955252c986d5c

Ecuación de reacción

O
water
O=C(NC(COCC1CCNCC1)c1ccccc1Cl)c1ccc2c(Cl)c[nH]c2c1
3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=S(=O)(OCC(F)(F)F)C(F)(F)F
2,2,2-trifluoroethyl trifluoromethane-sulfonate
O=C(NC(COCC1CCN(CC(F)(F)F)CC1)c1ccccc1Cl)c1ccc2c(Cl)c[nH]c2c1
title compound
Rendimiento 30.0%
O=C(NC(COCC1CCN(CC(F)(F)F)CC1)c1ccccc1Cl)c1ccc2c(Cl)c[nH]c2c1
3-Chloro-N-[1-(2-chlorophenyl)-2-[1-(2,2,2-trifluoroethyl)-piperidin-4-ylmethoxy]ethyl]-1H-indole-6-carboxamide
Rendimiento 30.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    Otrothe resulting precipitate was isolated by filtration
  3. 3
    OtroPurification of the filtrate (SiO2: 30% EtOAc in hexane)

Procedimiento

To a solution of 3-chloro-N-[1-(2-chlorophenyl)-2-(piperidin-4-ylmethoxy)ethyl]-1H-indole-6-carboxamide (700 mg, 1.6 mmol) in 5 mL of DMSO was added potassium carbonate (1.0 g, 7.9 mmol) and 2,2,2-trifluoroethyl trifluoromethane-sulfonate (364 mg, 1.6 mmol). The reaction was allowed to stir at room temperature overnight after which time water was added and the resulting precipitate was isolated by filtration. Purification of the filtrate (SiO2: 30% EtOAc in hexane) provided 250 mg (30%) of the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07427632B2uspto-grants-2008_09