607716-58-5Relevant articles and documents
Efficient synthesis of a GABAA α2,3-selective allosteric modulator via a sequential Pd-catalyzed cross-coupling approach
Jensen, Mark S.,Hoerrner, R. Scott,Li, Wenjie,Nelson, Dorian P.,Javadi, Gary J.,Dormer, Peter G.,Cai, Dongwei,Larsen, Robert D.
, p. 6034 - 6039 (2005)
A practical synthesis of 2-[3-(4-fluoro-3-pyridin-3-yl-phenyl)-imidazo[1,2- a]pyrimidin-7-yl]-propan-2-ol (1), an oral GABAA α 2/3-selective agonist, is described. The five-step process, which afforded 1 in 40% overall yield, included imidazopyrimidine 2 and pyridine boronic acid 4 as key fragments. The synthesis is highlighted by consecutive Pd-catalyzed coupling steps to assemble the final free base 1 in high yield and regioselectivity. A novel method for Pd removal in the final step is also described.