4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine → 1-(2-Chloro-3,6-difluorobenzyl)-7-[3-(morpholin-4-yl)phenyl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

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A mixture of 7-bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine (0.14 mmol, 51 mg), 3-morpholinophenylboronic acid pinacol ester (0.16 mmol, 46 mg), and Pd(PPh3)4 (0.015 mmol, 17 mg) was placed in a Schlenk tube. This tube was degassed via 3 cycles of vacuum—refill with N2. THF (3 mL, from sureseal bottle) and aqueous K2CO3 (2.0 M, 1 mL, degassed by bubbling with N2 for 10 min) was then added to the solid mixture in the Schlenk tube. The reaction was stopped after heating at 90° C. for 16 hrs. Extraction and concentration of combined organic layers gave a residue, which was purified on a silica gel column by using 6:1 ratio of CH2Cl2/MeOH (pre-saturated with ammonia gas) as eluents, furnishing 1-(2-chloro-3,6-difluorobenzyl)-7-[3-(morpholin-4-yl)phenyl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine in 61% yield (38 mg).

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