CP-293019 is a potent, selective antagonist of dopamine D4 receptor developed by Pfizer. The previous medicinal chemistry route commenced from 2,5-dipyridylmethyl ester 43 with the diamine intermediate accessed through hydrogenation and cyclization. After reduction, chiral resolution, epimerization, Mitsunobu reaction, and SNAr, a total of 12 steps were required to obtain the target molecule. Importantly, in the early stages of this program both diastereomers at C-X were targeted and evaluated. In contrast to this route, 15 could be smoothly coupled to glycine methyl ester followed by a non-diastereoselective Ni-electrocatalytic cross coupling of the corresponding alkyl iodide with RAE 40 (48%, 1:1 dr). Whereas the Weix group reported the chemical reductive coupling of alkyl bromides with RAEs, to our knowledge, this is the first example of a coupling between a secondary alkyl iodide and an RAE under electrochemical conditions. Finally, through a one-pot amide reduction and SNAr reaction, CP-293019 can be obtained in 7 steps. This pathway avoids chiral resolution, epimerization, and the use of expensive metal catalysts to deliver both diastereomeric series for biological evaluation.