Reaktion #48089

Reaktionsgleichung

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

Ausbeute 61.5%

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

Ausbeute 61.5%

Lösungsmittel

toluene

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted twice with ethylacetate
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered off
5. 5
   Einengenconcentrated under vacuo
6. 6
   SonstigeThe resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5)

Vorschrift

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)+.

Quelle