A scaleable synthesis of methyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate

…, BA Johns, CS Koble, N Kurose, MJ Sharp…

Index: Boros, Eric E.; Burova, Svetlana A.; Erickson, Greg A.; Johns, Brian A.; Koble, Cecilia S.; Kurose, Noriyuki; Sharp, Matthew J.; Tabet, Elie A.; Thompson, James B.; Toczko, Matthew A. Organic Process Research and Development, 2007 , vol. 11, # 5 p. 899 - 902

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Citation Number: 14

Abstract

A scaleable synthesis of methyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate (1b), starting from 5-bromo-2-methoxypyridine (8) and 4-fluorobenzaldehyde (9), is described. Key steps in the process include lithium–bromine exchange of 8, addition of the resulting lithiate to aldehyde 9, regioselective nitration of pyridone 12, and Pd-catalyzed alkoxycarbonylation of bromopyridine 15b. Overall yield of the five-stage synthesis was 23 ...