Diethyl Ether → HCID 22677378, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-acetamido-3,6-dichloropyridine-2-carboxylate (0.988 g, 4.0 mmol), ethoxyvinyltributyltin (2.70 mL, 8.0 mmol) and cesium fluoride (1.34 g, 8.8 mmol) in dioxane (20 mL) was sparged with nitrogen for 15 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.140 g, 0.2 mmol) was then added and the mixture was heated at 100° C. for 5 hours. After cooling, ether was added and the reaction mixture filtered through a silica plug. The solvents were removed and the crude product was purified by chromatography (ethyl acetate:hexane (1:2)) to give methyl 4-acetamido-3-chloro-6-(1-ethoxyvinyl)pryidine-2-carboxylate (0.780 g, 2.6 mmol). 1H NMR (CDCl3): δ 8.85 (s, 1H), 7.90 (br.s, 1H), 5.47 (d, J=2.0 Hz, 1H), 4.44 (d, J=2.0 Hz, 1H), 4.01 (s, 3H), 3.98 (q, J=7.0 Hz, 2H), 2.32 (s, 3H), 1.46 (t, J=7.0 Hz, 3H).

Provenance & Evidence