Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A

Autor: J. Fleck, Thomas, Jack Chen, Jiong, V. Lu, Cuong, J. Hanson, Kari
Zdroj: Organic Process Research & Development; March 2006, Vol. 10 Issue: 2 p334-338, 5p
Abstrakt: FeCl3 catalyzed an isomerization-free Friedel−Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer indole synthesis that effectively constructed both the indole core and side chain of the target molecule. The development of these methods enabled a rapid preparation of kilogram quantities of PHA-565272A.
Databáze: Supplemental Index