반응 #48089

반응 방정식

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

수율 61.5%

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

수율 61.5%

용매

toluene

water

water

반응 조건

후처리

1. 1
   추출extracted twice with ethylacetate
2. 2
   세척The combined organic layers were washed with brine
3. 3
   건조dried over magnesium sulfate
4. 4
   여과filtered off
5. 5
   농축concentrated under vacuo
6. 6
   기타The resulting residue was purified by flash column chromatography (Heptane/AcOEt:95/5)

실험 절차

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)+.

출처