Sodium Carbonate → 3'-(2-Fluoro-3-trifluoromethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 1-bromo-2-fluoro-3-trifluoromethylbenzene (0.424 g, 1.77 mmol), 5,5,5′,5′-tetramethyl-[2,2′]bi[1,3,2]dioxaborinanyl] (0.458 g, 2.03 mmol), 1,1′-bis(diphenylphosphino)ferrocene dichloropalladium (0.0632 g, 0.0774 mmol), and potassium acetate (0.499 g, 5.08 mmol) in DMF (10 mL), and purge with nitrogen for 0.5 hr. Heat for 2 hr. at 80° C. and cool to room temperature. Add 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.406 g, 1.36 mmol), sodium carbonate (4.0 mL of a 2M solution in water,) and bis(diphenylphosphino)ferrocene dichloropalladium (0.052 g, 0.0638 mmol). Heat the reaction at 80° C. for 20 hr. Purify by silica gel chromatography, eluting with 5:95 to 40:60 ethyl acetate:hexanes to give the 3′-(2-fluoro-3-trifluoromethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (0.102 g, 18%).

Provenance & Evidence