Regioselective Bromination of Thieno[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-one and Sequential Suzuki Couplings

Chunliang Lu; Minyu Dong; Hugh Y Zhu

doi:10.1021/acs.joc.7b01542

Regioselective Bromination of Thieno[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-one and Sequential Suzuki Couplings

J Org Chem. 2017 Sep 1;82(17):9229-9234. doi: 10.1021/acs.joc.7b01542. Epub 2017 Aug 16.

Authors

Chunliang Lu¹, Minyu Dong², Hugh Y Zhu¹

Affiliations

¹ Novartis Institutes for BioMedical Research (China) , Zhangjiang Hi-Tech Park, Shanghai 201203, China.
² Shanghai ChemPartner Co., Ltd. , Zhangjiang Hi-Tech Park, Shanghai 201203, China.

PMID: 28726406
DOI: 10.1021/acs.joc.7b01542

Abstract

Regioselective bromination of thieno[2',3':4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-one at the 2- or 9-position was achieved by modulating the basicity of the reaction conditions. An anion-directed site-specific bromination mechanism was proposed. In addition, a one-pot bromination-Suzuki coupling protocol was developed for quick access of analogues at the 9-position.