반응 #2151097

반응 방정식

1-(4-methylphenyl)piperazine

Xantphos

sodium tert-butoxide

5-bromo-2,2,7-trimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuran

→

title compound

수율 3.1%

1-[2,2,7-trimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]-4-(4-methylphenyl)piperazine

수율 3.1%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도under heated
3. 3
   온도reflux for 15 hours
4. 4
   여과the reaction solution was subjected to Celite filtration
5. 5
   workup.ADDITIONWater was added to the filtration, and extraction
6. 6
   기타The extract was dried
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   기타After that, the residue was purified by silica gel chromatography (hexane-ethyl acetate 10:1), and it
9. 9
   기타was crystallized from acetonitrile

실험 절차

To a solution of toluene (10 mL) containing 5-bromo-2,2,7-trimethyl-6-(4-methylphenyl)-2,3-dihydro-1-benzofuran (300 mg, 0.910 mmol) synthesized in Reference Example 157, 1-(4-methylphenyl)piperazine (160 mg, 0.910 mmol), Tris(dibenzylideneacetone)dipalladium (0) (24.9 mg, 0.027 mmol) and Xantphos (47.2 mg, 0.082 mmol), sodium tert-butoxide (131 mg, 1.36 mmol) was added, and the mixture was stirred under heated reflux for 15 hours. After cooled to room temperature, the reaction solution was subjected to Celite filtration. Water was added to the filtration, and extraction was performed using ethyl acetate. The extract was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After that, the residue was purified by silica gel chromatography (hexane-ethyl acetate 10:1), and it was crystallized from acetonitrile to obtain 12.0 mg of the title compound as a white solid (yield 3%).

출처