2-Hydroxy-6-bromopyridine, reaction

Due to the abundance of halopyridines, Suzuki reactions in which they serve as electrophiles have been used to synthesize a plethora of arylpyridines and heteroarylpyridines [39, 40]. 6-Phenyl-2-nitro-3-methylpyridine (55) was obtained via the reaction of 6-bromo-2-nitro-3-methylpyridine (54) and phenylboronic acid [39]. Not surprisingly, 3-chloropyridine was virtually inert under such conditions in contrast to 2-chloro- and 4-chloropyridine. The Suzuki coupling of 2-hydroxy-6-bromopyridine failed as well, possibly because 2-hydoxypyridines exist almost entirely in the keto form. 

Azimic acid (218) was synthesized in eleven steps from (25,65)-6-hydroxy-2-methyl-N-tosyl-A -piperidone-3 [497], (+)-Carpamic acid (219), along with 218, was synthesized using the same approach as for spicigerine methyl ester, 214 and 217, in which a Ni (II) catalyzed reaction is used to attach the side chain to a bromopyridine [495]. 

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