Reaktion #163384

Reaktionsgleichung

trifluoro-methanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester

4-tert.butylphenylacetylen

→

N-{2-[4-(4-tert-Butylphenylethynyl)-phenyl]-1-methyl-ethyl}-acetamide

Lösungsmittel

water

sec-butylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to r.t.
2. 2
   Sonstigeis then partitioned between EtOAc and citric acid (10% in water)
3. 3
   TrocknenThe organic layer is dried with Na2SO4
4. 4
   Sonstigethe solvent is removed in vacuo
5. 5
   SonstigeThe residue is purified twice by column chromatography (silica gel; DCM/MeOH 9/1 and aluminium oxide DCM/EtOAc 4/1)
6. 6
   SonstigeThe resulting product is triturated with MeOH

Vorschrift

To 0.50 g (1.54 mmol) trifluoro-methanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester (I53.2) and 0.32 g (2.00 mmol) 4-tert.butylphenylacetylen in 3.0 mL water and 3.0 mL sec-butylamine are added 0.10 g (0.14 mmol) bis(triphenyphosphine)dichloropalladium and the mixture is stirred at r.t. for 4 h and at 80° C. for 1 h. The reaction mixture is allowed to cool to r.t. and is then partitioned between EtOAc and citric acid (10% in water). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified twice by column chromatography (silica gel; DCM/MeOH 9/1 and aluminium oxide DCM/EtOAc 4/1). The resulting product is triturated with MeOH.

Quelle