Potassium Carbonate → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

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3-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (150 mg, 0.366 mmol, e.g. see Example 1 for methods of preparation) was dissolved in 1,4-dioxane (3 mL) and treated with trimethylboroxine (55.2 mg, 0.439 mmol, commercially available e.g. from Sigma-Aldrich or Thermo Fischer Scientific), potassium carbonate (76 mg, 0.549 mmol) and tetrakis(triphenylphosphine)palladium(0) (42.3 mg, 0.037 mmol). The reaction mixture, under argon, was heated at 110° C. for 20 hours. The mixture was then cooled, diluted with water and extracted with ethyl acetate (three times). The organic phase was dried and evaporated. The residue was purified on the mass-directed automated (preparative) HPLC (MDAP) and the residue was triturated with isohexane to give 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.028 g) as a white solid.

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