Cesium carbonate → Methyl 6-isopropenyl-5'-methyl-2,2'-bipyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-chloro-6-isopropenylisonicotinate (0.5 g, 2.36 mmol) in DMF (12 mL) were added 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.3 g, 5.9 mmol), palladium(II)acetate (26.5 mg, 0.12 mmol), cesium carbonate (1.54 g, 4.72 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.13 g, 0.24 mmol) and copper(I) chloride (0.23 g, 2.36 mmol). The mixture was purged with argon and heated to 100° C. After 45 min, saturated aqueous NaHCO3 was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (0.55 g). MS 269.1 (M+1).

Provenance & Evidence