ORGN 679 |
| Thienopyridine 4 is a known AMPK activator. However, we recently were unable to repeat the reported synthesis of 4, using the procedure described in the patent literature, which led us to develop an improved procedure. The key features in the synthesis of thienopyridine 4 involve (1) preparation of tri-substituted thiophene 1; (2) coupling of 1 with cyanoacetic acid to produce amide 2; (3) base-induced cyclization of 2 to provide the fused thienopyridine 3; and finally, (4) installation of the 2-hydroxyphenyl group by Suzuki coupling to give the biphenyl-substituted thienopyridine 4. In particular, the choice of coupling conditions for the preparation of 2 and the choice of base for the cyclization of 2 to 3 are critical for the successful production of thienopyridine 4.
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Biologically-Related Molecules and Processes
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258B, Oral
Division of Organic Chemistry |
