Morpholine → Methyl 3-methyl-5-(morpholin-4-yl)-1-benzofuran-2-carboxylate

Participants

Reaction Steps

To a solution (100 mL) of methyl 5-bromo-3-methyl-1-benzofuran-2-carboxylate (5.4 g) synthesized in the above-mentioned (1) in toluene were added morpholine (5.2 mL), cesium carbonate (13.0 g), tris(dibenzylideneacetone)dipalladium (0) (0.92 g) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.1 g), and the mixture was heated under reflux under argon atmosphere for 20 hr. The reaction mixture was cooled to room temperature, and filtered through celite. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.69 g, 13%) as a yellow oil.

Provenance & Evidence