Potassium Carbonate → 4-(1-Methyl-1H-pyrazol-4-ylmethyl)-3'-(2,3-difluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

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Reaction Steps

Dissolve 3′-chloro-4-(1-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (160 mg, 0.55 mmol) in N,N-dimethylacetamide (4 mL) and water (2 mL) and purge with nitrogen for 0.5 hr. Add potassium carbonate (180 mg, 1.30 mmol) then 2,3-difluorobenzeneboronic acid (100 mg, 0.66 mmol) and purge with nitrogen for 0.5 hr. Add tetrakis(triphenylphosphine)palladium(0) (0.01 g, 0.0086 mmol) and heat at 110° C. for 3.25 hr. Cool to room temperature and purify (silica gel chromatography, eluting with 0:100 to 30:70 methanol:DCM), followed by reverse phase HPLC to give the title compound (52.69 mg, 26%). MS (ES): m/z=371 [M+H]+.

Provenance & Evidence