Reaktion #336
ord-89890e81ad5d4e12a61d2ee591f39e46
Reaktionsgleichung
Lösungsmittel
Reaktionsbedingungen
Vorschrift
tert-butyl 5-bromonicotinate (1.4 g, 5.42 mmol), morpholine (0.591 ml, 6.78 mmol), cesium carbonate (3.53 g, 10.85 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.507 g, 0.81 mmol) were dissolved in toluene (20 ml). The reaction flask was purged with nitrogen and diacetoxypalladium (0.061 g, 0.27 mmol) was added. The resulting suspension was stirred at 80 °C for 5 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 5-morpholinonicotinate (0.381 g, 26.6 %) as a yellow oil which solidified on standing.