Reacción #69470

Ecuación de reacción

methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

1-bromo-3-fluorobenzene

cesium carbonate

→

methyl 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate

Rendimiento 79.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting suspension was degassed with argon
2. 2
   Temperaturato cool to room temperature
3. 3
   Otrothe crude product was purified by flash chromatography on silica gel eluting with 0 to 7% propanol in DCM
4. 4
   OtroThe solvent was evaporated to dryness

Procedimiento

Diacetoxypalladium (3.3 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]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 (3.3 mL). The resulting suspension was degassed with argon and then stirred at 100° C. for 20 h. The reaction mixture was allowed to cool to room temperature, and the crude product was purified by flash chromatography on silica gel eluting with 0 to 7% propanol in DCM. The solvent was evaporated to dryness to afford methyl 8-[(2R)-(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. Mass Spectrum: m/z [M+H]+=453.

Fuente