Development of a Scalable Synthesis of GSK183390A, a PPAR Α/γ Agonist

A scalable synthesis of GSK183390A, a PPAR alpha/gamma agonist, is described. This synthesis is highlighted by (1) a regioselective formal 1,3-dipolar cycloaddition reaction between an enamine and a nitrile imine dipole to form a 1,3,5-trisubstituted pyrazole and (2) a regioselective amidomethylation of an o-cresol derivative using 2-chloro-N-hydroxymethylacetamide.