  7-Azaindole is the core of numerous pharmaceuticals for which C-2 and C-6 derivatives are known to function as anti-cancer or analgesics respectively. Current methods of 7-azaindole functionalization are limited, requiring stoichiometric introduction of directed metalation groups (DMGs), which may be resistant to further manipulation or removal (Fagnou, K. et al. Org. Lett. 2009  , 11, 1357; Snieckus, V. et al. Angew. Chem. Int. Ed. 2012  , 51, 2722). This project focuses on the regioselective functionalization of the C-2 and C-6 positions of the 7-azaindole scaffold (ortho to the respective nitrogens) by directed ortho metalation, utilizing migratable DMGs. In preliminary studies, the N-to-N [1,3]-DMG migration has been realized (Snieckus, V. et al. unpublished). The application of this concept will allow the multiple use of the same DMG for regioselective functionalization, followed by its removal or derivitization.

Dancing directed metalation groups: Regioselective functionalization of azaindoles

248th National Meeting (2014)

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