반응 #74113

반응 방정식

racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphtalene

sodium tertbutoxide

benzophenonimine

4-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine

→

title compound

수율 65.0%

N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]aniline

수율 65.0%

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was refluxed for 3 hours
2. 2
   여과was filtered over a celite pad
3. 3
   기타the solvent evaporated
4. 4
   workup.DISSOLUTIONThe residue was redissolved with ethylacetate
5. 5
   세척washed with water
6. 6
   건조The organic layer was dried over Na2SO4
7. 7
   기타evaporated again to dryness
8. 8
   기타The crude was purified by chromatography on a silica gel column
9. 9
   세척eluted by dichloromethane-methanol 95/5

실험 절차

1.9 g (4.5 mmol) of 4-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine were dissolved in 60 ml of dry toluene under nitrogen atmosphere and 366 mg (0.4 mmol) of tris(dibenzylidene-acetone)dipalladium(0), 498 mg (0.8 mmol) of racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphtalene, 562 mg (5.85 mmol) of sodium tertbutoxide and 975 L (5.85 mmol) of benzophenonimine were added to the solution successively. The mixture was refluxed for 3 hours. After cooling to room temperature the reaction mixture was filtered over a celite pad and the solvent evaporated. The residue was redissolved with ethylacetate and washed with water. The organic layer was dried over Na2SO4 and evaporated again to dryness. The crude was purified by chromatography on a silica gel column eluted by dichloromethane-methanol 95/5, affording 1.5 g (65% yield) of the title compound.

출처