1-Bromo-3,5-difluorobenzene → methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

diacetoxypalladium (0.028 g, 0.13 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (0.9 g, 2.51 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.145 g, 0.25 mmol), 1-bromo-3,5-difluorobenzene (0.361 ml, 3.14 mmol) and cesium carbonate (1.227 g, 3.77 mmol) suspended in 1,4-dioxane (16.05 ml). The resulting suspension was degased with argon and then stirred at 100 °C (18:00) for 15 hours. The reaction mixture was allowed to cool to room temperature, concentrated in presence of silica gel and purified by flash chromatography on silica gel eluting with 0 to 10% methanol in ethyl acetate. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (0.792 g, 67.0 %) as an yellow foam.

Provenance & Evidence