1334785-10-2Relevant articles and documents
Spiroazetidine-piperidine bromoindane as a key modular template to access a variety of compounds via C-C and C-N bond-forming reactions
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.
, p. 6351 - 6354,4 (2012/12/12)
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.