Sulfuric Acid → HCID 67342412, compound

2-(Piperidinyl)pyridines 83 are prepared as described in Scheme 22. Strong base, such as n-BuLi, in a solvent such as dry THF, is added to dibromopyridine 77 at a temperature less than RT, preferably below about −50° C., more preferably at about −70° C. 4-Methylpiperidone is added to form the 4-hydroxy-piperidine 80 at a temperature less than RT, preferably below about −50° C., more preferably at about −70° C. The 4-hydroxy piperidine 80 is hydrated, such as with strong acid, preferably H2SO4, at a temperature above RT, preferably above 750C, more preferably at about 100 C., to form the tetrahydro-bipyridine 81. The 2-bromo-pyridine 81 is aminated, such as with NH4OH, in the presence of Cu powder at a temperature above RT, preferably above about 75° C., more preferably at about 100° C., to form the amino-pyridine 82. Preferably the reaction is run in a sealed tube. The 1′,2,3′,6′-tetrahdyro-[2,4′]bipyridinyl-6-ylamine is hydrogenated, such as with H2 in the presence of Pd(OH)2/C, at a temperature of about RT, to form the piperidinyl pyridine 83.

1. custommore preferably at about −70° C

ORD record

ord-6c5762a2eb5f4fe183d60a9c96b47f60

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06645990B2