Date of Award
7-1-2016
Degree Type
Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
Advisor(s)
Daniel A. Clark
Keywords
3-amino-4-chloropyridine, imidazopyridine, Reductive Amination
Subject Categories
Physical Sciences and Mathematics
Abstract
The following describes a protocol for the one-pot deprotection and reductive amination of N-Boc-3-amino-4-halopyridines. The intermediate 3-amino-4-chloropyridinium trifluoroacetate salt combined with trimethylsilyl trifluoromethanesulfonate (TMSOTf) effectively facilitates condensation with a carbonyl moiety. The corresponding imine is subsequently reduced using sodium triacetoxyborohydride. The product, N-alkyl-3-amino-4-halopyridines, provides an effective synthon for our previously reported synthesis of imidazo[4,5-c]pyridines. The current approach greatly improves upon previously alkylation methods of these aryl amines; providing an expanded substrate scope with excellent yields.
Access
Open Access
Recommended Citation
Wilhelmsen, Christopher Alexander, "Deprotection and Reductive Amination Methodology of N-Boc-3-amino-4-halopyridines" (2016). Dissertations - ALL. 506.
https://surface.syr.edu/etd/506
