CPC C07D 279/08 (2013.01) [C07D 491/113 (2013.01)] | 20 Claims |
1. A method for forming a deuterated compound of Formula IA, IB, or IC:
or an azoxy dimer or salt thereof;
wherein
R1 is 2-(C1-C6)alkyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl or 4-((C3-C6)cycloalkyl methyl)piperazin-1-yl;
R2 is halo, cyano, —(C1-C3)alkyl, or —O(C1-C3)alkyl, wherein —(C1-C3)alkyl or —O(C1-C3)alkyl has 2 to 7 halo substituents;
R3 and R4 are independently H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl; and
R5 is H, D, halo, hydroxyl, cyano, —(C1-C6)alkyl;
comprising:
a) reacting a deuteride reducing agent and a compound of Formula IA wherein R3 and R4 are H to form a reduced intermediate; and
b) reacting the reduced intermediate and an oxidizing agent to form a compound of Formula IA wherein at least one of R3 or R4 is D; or
c) reacting the reduced intermediate and a protic reagent to form a compound of Formula IB or IC;
wherein the deuterated compound of Formula IA, IB, or IC is thereby formed.
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