Isomerization-free sulfonylation and its application in the synthesis of PHA-565272A

…, JJ Chen, CV Lu, KJ Hanson

Index: Fleck, Thomas J.; Chen, Jiong Jack; Lu, Cuong V.; Hanson, Kari J. Organic Process Research and Development, 2006 , vol. 10, # 2 p. 334 - 338

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Abstract

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 ...