Potassium Carbonate → 3-Pyridinecarboxylic acid, 5,6-dimethyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 5-bromo-6-chloro-3-pyridinecarboxylate (595 mg, 2.375 mmol), tetrakis(triphenylphosphine)palladium (0) (275 mg, 0.238 mmol) and K2CO3 (492 mg, 3.56 mmol) in dioxane (6.5 ml), trimethylboroxin (1.328 ml, 9.50 mmol) was added under argon. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was allowed to cool down, filtered through a pad of silica, and concentrated to give 857 mg of the crude material. Purification by flash chromatography using Flashmaster II, a 20 g silica gel cartridge, and mixtures of hexane and EtOAc as eluent afforded 276 mg of desired compound.

Provenance & Evidence