Novel 2,4,5-Trisubstituted Pyridines as Key Intermediates for the Preparation of the TSPO Ligand 6-F-PBR28: Synthesis and Full 1H and C-13 NMR Characterization

作者：Damont Annelaure^*; Lemee Frederic; Raggiri Guillaume; Dolle Frederic

来源：Journal of Heterocyclic Chemistry, 2014, 51(2): 404-410.

DOI：10.1002/jhet.1723

As part of our ongoing research for molecular structures binding to the translocator protein (TSPO 18kDa), we investigated the preparation of a number of new 2,4,5-trisubstituted pyridines as novel building blocks. In particular, 5-amino-2-halo-4-phenoxypyridines (11, 12, 13) were designed as key intermediates for the synthesis of the recently developed TSPO ligand 6-F-PBR28 and its fluorine-18-labeled version for positron emission tomography, 6-[F-18]F-PBR28. We hereby report the chemical preparation as well as the H-1 and C-13 NMR spectroscopic data of polysubstituted pyridines 2, 3, 4, 5, 6, 7, 7b, 8, 9, 10, 11, 12, 13, 14. The latter demonstrates dramatic changes in electron density repartition of the aromatic ring upon substitution.

• 出版日期2014-3
• 单位中国地震局