Zindoxifene

Originator

Zindoxifene,GASTHAUS

Definition

ChEBI: Zindoxifene is a phenylindole.

Manufacturing Process

At 70°C there were added BBr 3 with the injector into a solution of 1-methyl-2- (4-methoxy-phenyl)-6-methoxy-1-ethylindole in water free methylene chloride. After 30 min the cold bath was removed and the mixture stirred overnight. The reaction mixture is carefully poured into a saturated sodium bicarbonate solution with ice cooling. The product is extracted three times with ethyl acetate, the combined organic extracts washed with sodium bicarbonate solution and water, dried and the solvent removed on a rotary evaporator. The 3-methyl-2-(4-hydroxyphenyl)-6-hydroxy-1-ethylindole was produced, melting point 142-143°C.
There are added acetic anhydride and of pyridine to the thus obtained 3- methyl-2-(4-hydroxyphenyl)-6-hydroxy-1-ethylindole and the mixture heated for 2 h at the boiling point. After cooling the mixture is poured onto ice, extracted with methylene chloride and the organic phase washed twice with 2 N HCl. After drying and removal of solvent in the rotary evaporator the residue is chromatographed with methylene chloride via silica and subsequently 3-methyl-2-(4-acetoxyphenyl)-6-acetoxy-1-ethylindole is obtained, melting point 150-152°C (recrystallized from ethanol).

Therapeutic Function

Antiestrogen