Methyl 6-chloro-5'-methyl-3,3'-bipyridine-5-carboxylate → Methyl 6-cyclopentyl-5'-methyl-3,3'-bipyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5′-methyl-3,3′-bipyridine-5-carboxylate (6-1, 0.15 g, 0.57 mmol, 1.0 equiv, prepared in an analogous fashion to Examples 2 and 8) in dioxane (2.9 mL) at 25° C. was added cyclopentylzinc bromide (3.43 mL, 1.71 mmol, 3.0 equiv, 0.5 M in THF) and tetrakis(triphenylphosphine)palladium(0) (0.099 g, 0.086 mmol, 0.15 equiv). The reaction mixture was heated for 3 h at 90° C. The reaction mixture was cooled partitioned between water (10 mL) and EtOAc (30 mL), washed with water (3×30 mL) and brine (1×30 mL), and the organic phase was dried over magnesium sulfate. The residue was purified via normal phase chromatography (5 to 100% EtOAc in hexanes, silica) to afford the desired product (6-2) as an oil after concentration. ESI+MS [M+H]+ C18H20N2O2 calc'd 297.2, found 297.1

Provenance & Evidence