Reacción #9765

ord-0d961a5452df42c8855de61b7e83107b

Ecuación de reacción

Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O
2-(4-hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one
Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O
intermediate 105
Cc1cc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1O
2-(4-hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one
O=C([O-])[O-].[Cs+].[Cs+]
caesium carbonate
CCOC(=O)CBr
ethyl bromoacetate
CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C
title compound
CCOC(=O)COc1ccc(C(C)(C)C(=O)c2sc(-c3ccc(C(F)(F)F)cc3)cc2C)cc1C
ethyl[4-(1,1-dimethyl-2-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}-2-oxoethyl)-2-methylphenoxy]acetate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe solid residue was filtered
  2. 2
    Concentraciónthe filtrate was concentrated in vacuo
  3. 3
    Otrothe residue purified by flash column chromatography
  4. 4
    Lavadoeluting with 1% EtOAc/cyclohexane

Procedimiento

To a solution of 2-(4-hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one (intermediate 105, 62.0 mg) in anhydrous acetonitrile (2 ml) was added caesium carbonate (106 mg) and ethyl bromoacetate (18 μl) and the reaction stirred at room temperature under nitrogen for 20 hours. The solid residue was filtered, and the filtrate was concentrated in vacuo and the residue purified by flash column chromatography, eluting with 1% EtOAc/cyclohexane yielded the title compound as a white solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07091237B2uspto-grants-2006_08