Carboxylation reaction of a highly functionalized vinylic anion: a case of unexpected stability and reactivity

Attempts to prepare JNJ 26273364, a highly functionalized pyrazole-based CCK1 receptor antagonist, using a carboxylation reaction led to a series of unexpected results. This work demonstrated the unique reactivity and stability of the highly functionalized Z-alkene functionality present around the pyrazole.

Attempts to prepare JNJ 26273364, a highly functionalized pyrazole-based CCK1 receptor antagonist, using a carboxylation reaction led to a series of unexpected results. This work demonstrated the unique reactivity and stability of the highly functionalized Z-alkene functionality present around the pyrazole.