Reaktion #74113

Reaktionsgleichung

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

Ausbeute 65.0%

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

Ausbeute 65.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 3 hours
2. 2
   Filtrationwas filtered over a celite pad
3. 3
   Sonstigethe solvent evaporated
4. 4
   workup.DISSOLUTIONThe residue was redissolved with ethylacetate
5. 5
   Waschenwashed with water
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Sonstigeevaporated again to dryness
8. 8
   SonstigeThe crude was purified by chromatography on a silica gel column
9. 9
   Wascheneluted by dichloromethane-methanol 95/5

Vorschrift

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.

Quelle