Potassium Carbonate → Pyridine-3-sulfonic acid {2-[3'-(4-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochloride

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Dissolve pyridine-3-sulfonic acid [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-amide (0.200 g, 0.504 mmol) in DMA-H2O (4 mL; 3:1 v/v, previously degassed with nitrogen). Add 4-fluorophenyl boronic acid (0.084 g, 0.605 mmol), potassium carbonate (0.167 g, 1.209 mmol) and tetrakis(triphenyl-phosphine)palladium (0.029 g, 0.025 mmol). Stir the reaction mixture at 110° C. for 18 hr. Cool and dilute with ethyl acetate and water. Extract the aqueous layer with ethyl acetate and combine the organic layers. Dry the organics over sodium sulfate, filter, and concentrate. Purify by SCX chromatography, eluting with dichloromethane, dichloromethane:methanol, methanol, and 1N ammonia in methanol. Purify by silica gel chromatography eluting with hexanes:acetone 1:1 to afford the free base of the title compound (0.136 g, 59% yield).

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