2-(Tributylstannyl)pyridine → Methyl 1-methyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylate

Participants

Reaction Steps

Methyl 5-bromo-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (57 mg, 0.23 mmol), 2-(tributylstannyl)pyridine (85 mg, 0.23 mmol) and tetrakis(triphenylphosphine)palladium (13 mg, 0.012 mmol, Strem) were stirred in 1.5 mL of dioxane at 90° C. for 16 h. The reaction mixture was cooled to RT, diluted with H2O and extracted with EtOAc (2×). The combined organic extracts were washed 1× with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude residue by column chromatography (4 g pre-packed column, elution 0-30% EtOAc/Hexanes) gave the title compound (22 mg, 39%) as a light yellow solid. MS m/z: 245 (M+1).

Provenance & Evidence