Water → 4-(1,3-Dimethyl-1H-pyrazol-4-ylmethyl)-3'-(2-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

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Reaction Conditions

Reaction Steps

Add 2-fluorobenzeneboronic acid (215 mg, 1.5 mmol) to a nitrogen purged solution of 3′-chloro-4-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (200 mg, 0.65 mmol) in dry N,N-dimethylacetamide (4 mL), deoxygenated water (2 mL), potassium carbonate (215 mg, 1.72 mmol), tetrakis(triphenylphosphine)palladium(0) (0.004 g, 0.0035 mmol) and stir at 110° C. for 16 hr. Cool to room temperature, add water (10 mL) and extract with DCM (3×20 mL). Concentrate the combined DCM extracts and purify by reverse phase HPLC to give the title compound (0.130 g, 54%). MS (ES): m/z=367 [M+H]+.

Provenance & Evidence