Synthesis of 6-SF-indazoles and an SF-analog of gamendazole.

This work describes an efficient synthetic approach for a new type of SF5-substituted heterocyclic system, namely 6-SF5-indazoles. During this study, various derivatives of 6-SF5-indazoles such as bromo, iodo, nitro, N-acetyl and N-benzyl substituted compounds were synthesized and characterized. In addition, the utility of the synthetic methodology was demonstrated via the synthesis of 6-SF5-gamendazole - a fully matched analog of the experimental male contraceptive gamendazole, which has a 6-CF3-substituted indazole core.