Reaktion #69464

Reaktionsgleichung

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

1-bromo-3,5-difluorobenzene

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

cesium carbonate

→

methyl 8-[(2R)-1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-4-oxo-chromene-6-carboxylate

Ausbeute 67.1%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting suspension was degassed with argon
2. 2
   Temperaturto cool to room temperature
3. 3
   Einengenconcentrated in presence of silica gel
4. 4
   Sonstigepurified by flash chromatography on silica gel eluting with 0 to 10% MeOH in EtAc
5. 5
   SonstigeThe solvent was evaporated to dryness

Vorschrift

Diacetoxypalladium (0.028 g, 0.13 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (0.9 g, 2.51 mmol), 1-bromo-3,5-difluorobenzene (0.361 ml, 3.14 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (145 mg, 0.25 mmol) and cesium carbonate (1.227 g, 3.77 mmol) dissolved in 1,4-dioxane (16 mL). The resulting suspension was degassed with argon and then stirred at 100° C. for 15 h. 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% MeOH in EtAc. The solvent was evaporated to dryness to afford methyl 8-[(2R)-1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-4-oxo-chromene-6-carboxylate (0.792 g, 67%) as an yellow foam. Mass Spectrum: m/z [M+H]+=471.

Quelle