An intra/intermolecular suzuki sequence to benzopyridyloxepines containing geometrically pure exocyclic tetrasubstituted alkenes.
A route to enable the preparation of 5-benzylidenyl-benzopyridyloxepine analogues was developed to continue our research in the field of nuclear hormone receptor modulators. The key steps are 1) a syn-stereoselective diboration of a tethered aryl alkyne; 2) an intramolecular Suzuki cross-coupling reaction, which forms in a stereo- and regiocontrolled fashion, the 5-exoalkylidenyl 7-membered ring imbedded within the core of the scaffold and; 3) an intermolecular Suzuki to furnish the final tetra-substituted olefinic benzopyridyloxepines.
Carson
Matthew W
MW
Discovery Chemistry Research and Technology, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, USA. carsonma@lilly.com
Giese
Matthew W
MW
Coghlan
Michael J
MJ
D000480:Alkynes / Q000737:chemistry*; D001584:Benzoxepins / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
D000480:Alkynes; D001584:Benzoxepins; D001965:Bromides; D011725:Pyridines; C023666:pyridine