Morpholine → HCID 57422999, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (3.78 g, 11.61 mmol), methyl 5-bromo-2-chloro-4-methoxybenzoate (2.317 g, 8.29 mmol), palladium(II) acetate (0.037 g, 0.17 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.206 g, 0.33 mmol) were combined and evacuated and purged with nitrogen (3 times). Degassed toluene (30 mL) and morpholine (0.723 mL, 8.29 mmol) was added and the resulting suspension was evacuated and purged with nitrogen several times. The reaction mixture was heated to 100 °C under nitrogen for 22 hours. The reaction was allowed to cool to ambient temperature and filtered through a celite pad, washing with EtOAc. The filtrate was concentrated and the crude product purified by flash silica chromatography, elution gradient 10 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-chloro-4-methoxy-5-morpholinobenzoate (1.865 g, 79 %) as a cream crystalline solid.

Provenance & Evidence