Use of fluorine-containing stationary phases for the separation of an alkyl bromide from its hydrocarbon analog by high-performance liquid chromatography

Radiolabelled Sch 13835, an inhibitor of platelet derived growth factor, was prepared by catalytic hydrogenolysis of a benzyl bromide precursor with tritium gas. Regular and deactivated reversed-phase HPLC stationary phases gave poor peak shapes and little resolution of Sch 13835 and the benzyl bromide precursor. Fluorodecyl and fluoroether stationary phases in the analytical reversed-phase mode gave baseline separation using organic-aqueous (no buffers) mobile phases. Elution orders were reversed on either phase by a change in the organic component from methanol to acetonitrile. The product is unstable in aqueous (or Other protic) Solvents, forming a ring-opened acid. Conditions were developed to successfully purify the compound by reversed-phase HPLC with minimal decomposition. A second analytical HPLC assay was developed using normal-phase Solvents on a fluoroether stationary phase.