Chemistry
Heterocyclic Building Blocks
Pyridines
6-bromopyridin-3-amine
Nucleophilic substitution: The bromine atom can be substituted by a nucleophile, such as a primary or secondary amine, in the presence of a suitable base or catalyst.
Reductive amination: The amine group can undergo reductive amination with an appropriate carbonyl compound, such as an aldehyde or a ketone, in the presence of a reducing agent like sodium cyanoborohydride or sodium triacetoxyborohydride, to form secondary or tertiary amines.
Acylation: The amine group can undergo acylation with acyl chlorides or acid anhydrides to form amides.
Suzuki coupling: The bromine atom can undergo Suzuki coupling reaction with boronic acids or boronate esters in the presence of a palladium catalyst to form biaryl compounds.
Metalation: The pyridine ring can be metalated at the 3-position using strong bases like butyllithium or lithium diisopropylamide (LDA), followed by reaction with various electrophiles to introduce different functional groups.
Halogenation: The pyridine ring can undergo further halogenation reactions at positions ortho, meta, or para to the amine and bromine groups under appropriate conditions.
Reduction: The bromine atom can be reduced to a bromide ion using reducing agents such as hydrogen gas with a suitable catalyst (e.g., palladium on carbon), or with reagents like sodium borohydride.
Framework+−
By Key Group+−
By Parent Nucleus+−
By Functional Group+−
Heterocyclic related+−
Formula Weight+−