Potassium Carbonate → Methyl 6-chloro-5-methylpyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 5-bromo-6-chloro-3-pyridinecarboxylate (400 mg, 1.597 mmol), tetrakis(triphenylphosphine)palladium (0) (185 mg, 0.160 mmol), and K2CO3 (331 mg, 2.395 mmol) in dioxane (5 ml), trimethylboroxin (0.446 ml, 3.19 mmol) was added under argon. The reaction mixture was heated at 110° C. for 5 h. The reaction mixture was allowed to cool down, filtered through a pad of silica, and concentrated to give 176 mg of the crude material. Purification by flash chromatography using Flashmaster II, a 5 g spherical silica gel cartridge, and mixtures of hexane and DCM as eluent afforded 76 mg of desired compound and 84 mg of methyl 6-chloro-5-methyl-3-pyridinecarboxylate as by-product.

Provenance & Evidence