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 (3.33 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (121 mg, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.61 mg, 0.03 mmol), 1-bromo-3-fluorobenzene (0.047 ml, 0.42 mmol) and cesium carbonate (165 mg, 0.51 mmol) suspended in 1,4-dioxane (3.329 ml). The resulting suspension was degased with argon and then stirred at 100 °C for 20 hours _(_ _UPLC/MS O/N showed that the SM was almost consumed)._ The reaction mixture was allowed to cool to room temperature, the crude product was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 0 to 7% Propanol-CH2Cl2. The solvent was evaporated to dryness to afford methyl 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (120 mg, 79 %) as a yellow oil which solidified on standing.

Provenance & Evidence