Spiroazetidine–piperidine bromoindane as a key modular template to access a variety of compounds via C–C and C–N bond-forming reactions

In the context of our ghrelin inverse agonist program, a functionalized bromoindane 3 provided a versatile intermediate for structure–activity relationship studies. After developing operationally simple cross-coupling reactions, a broad spectrum of chemical space was successfully explored. Optimizat...

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Bibliographic Details
Published in:Tetrahedron letters 2012-11, Vol.53 (47), p.6351-6354
Main Authors: Fernando, Dilinie P., Jiao, Wenhua, Polivkova, Jana, Xiao, Jun, Coffey, Steven B., Rose, Colin, Londregan, Allyn, Saenz, James, Beveridge, Ramsay, Zhang, Yingxin, Storer, Gregory E., Vrieze, Derek, Erasga, Noe, Jones, Ryan, Khot, Vishal, Cameron, Kimberly O., McClure, Kim F., Bhattacharya, Samit K., Orr, Suvi T.M.
Format: Article
Language:English
Subjects:
Bromoindane
Cross-coupling
Heterocycle
Spiroazetidine–piperidine
Suzuki
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Summary:In the context of our ghrelin inverse agonist program, a functionalized bromoindane 3 provided a versatile intermediate for structure–activity relationship studies. After developing operationally simple cross-coupling reactions, a broad spectrum of chemical space was successfully explored. Optimization of a one-pot borylation/Suzuki sequence provided the desired products in high yield with low loading of the palladium catalyst. High yields of N-linked heterocyclic analogues were obtained through palladium catalyzed C–N bond formation. In addition, carboxylation of the bromoindane provided an indane carboxylic acid for further diversification.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.09.047