1-Bromo-3-fluorobenzene → Methyl 8-[1-(3-fluorophenyl)pyrrolidin-2-yl]-2-morpholin-4-yl-4-oxochromene-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

diacetoxypalladium (0.045 g, 0.20 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (1.8 g, 5.02 mmol), methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (1.8 g, 5.02 mmol) and cesium carbonate (2.455 g, 7.53 mmol) dissolved in 1,4-dioxane (35 ml). The resulting suspension was degased with argon and then stirred at 100 °C for 11 hours. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 20% methanol in ethyl acetate (on 50 min). The solvent was evaporated to dryness to afford methyl 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (1.610 g, 70.8 %) as a clear yellow foam.

Provenance & Evidence