Reaction #48089

Reaction equation

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

Yield 61.5%

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

Yield 61.5%

Solvents

toluene

water

water

Conditions

Workup

1. 1
   Extractionextracted twice with ethylacetate
2. 2
   WashThe combined organic layers were washed with brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Filtrationfiltered off
5. 5
   Concentrationconcentrated under vacuo
6. 6
   OtherThe resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5)

Procedure

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)+.

Source