Reacción #48089

Ecuación de reacción

3-bromo-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide

tri-potassium phosphate

tricyclohexylphosphine

ethylboronic acid

→

yellow solid

Rendimiento 61.5%

N-(4-tert-butyl-benzyl)-3-chloro-5-ethyl-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide

Rendimiento 61.5%

Disolventes

toluene

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ethylacetate
2. 2
   LavadoThe combined organic layers were washed with brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered off
5. 5
   Concentraciónconcentrated under vacuo
6. 6
   OtroThe resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5)

Procedimiento

285 mg of 3-bromo-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-fluoro-5-trifluoromethyl-phenyl)-ethyl]-benzamide (0.6 mmol, Example B177), 44 mg of ethylboronic acid (1.75 mmol), 371 mg of tri-potassium phosphate (0.05 mmol), 14 mg of tricyclohexylphosphine and 6 mg of palladium acetate were suspended in 2.3 ml toluene and 0.1 ml water and stirred at 100° C. for 3.5 h under nitrogen. The reaction mixture was then cooled down to RT, diluted with 4 ml water and extracted twice with ethylacetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered off and concentrated under vacuo. The resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5) to yield 192 mg of a yellow solid. MS (ISP) 520.3 (M+H)+.

Fuente