Electrophilic ring fluorination of 3,5-disubstituted pyrazoles: application to the formal synthesis of a neprilysin inhibitor key intermediate†‡
Gérard Guillamot,Phannarath Phansavath,Virginie Ratovelomanana-Vidal
New Journal of Chemistry Pub Date : 11/16/2020 00:00:00 , DOI:10.1039/D0NJ05222A
Abstract

The access to a new family of unusual 4-fluorinated pyrazoles bearing acetal moities at the 3- or 5-position has been achieved by electrophilic fluorination using Selectfluor® with yields up to 67%. The unconverted starting material can be recovered and recycled. This reaction has been successfully applied to the formal synthesis of a key intermediate in the synthesis of neprilysin inhibitors with 42% overall yield (5 steps).

Graphical abstract: Electrophilic ring fluorination of 3,5-disubstituted pyrazoles: application to the formal synthesis of a neprilysin inhibitor key intermediate