Hydrochloric Acid → Ethyl 2,4-diethylpyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-bromo-4-chloropyridine-3-carboxylate (2.0 g, 7.6 mmol) was dissolved in anhydrous dioxane (55 mL). A solution of diethyl zinc (6.9 mL, 7.6 mmol, 1.1 M in toluene) was added dropwise, and then was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (83 mg, 113 μmol). The mixture was heated at 70° C. for 6 hours, and water followed by 1 N HCl was added. The mixture was extracted 3 times with ethyl acetate, and the combined organic phases were washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-20% hexane/ethyl acetate to afford ethyl 2,4-diethylpyridine-3-carboxylate (720 mg, 46% yield).

Provenance & Evidence