تفاعل #537

ord-e061647f5f0c433f84efb82229734131

معادلة التفاعل

Fc1cc(F)cc(Br)c1
Fc1cc(F)cc(Br)c1
COC(=O)c1cc(C2CCCN2)c2oc(N3CCOCC3)cc(=O)c2c1
COC(=O)c1cc(C2CCCN2)
COC(=O)c1cc(C2CCCN2c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1
COC(=O)c1cc(C2CCCN2c
المردود 52.2%

المذيبات

ظروف التفاعل

درجة الحرارة
100°CELSIUS

الإجراء التجريبي

diacetoxypalladium (6.26 mg, 0.03 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxylate (200 mg, 0.56 mmol), 1-bromo-3,5-difluorobenzene (0.080 ml, 0.70 mmol) and cesium carbonate (273 mg, 0.84 mmol) dissolved in 1,4-dioxane (8 ml). The resulting suspension was degased with argon and then stirred at 100 °C (15:00) for 18 hours. The reaction mixture was allowed to cool to room temperature, filtered and concentrated. The crude product was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 0 to 6% 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 (137 mg, 52.2 %) as a clear yellow foam. LCMS and NMR are OK.

المصدر

750 AstraZeneca ELN dataset