4-(4-Bromo-2-nitrophenyl)morpholine (500 mg, 1741 μmol) and morpholine (303 μL, 3483 μmol) were dissolved in toluene (71047 μL, 666992 μmol). To the stirred mixture was added X-Phos (125 mg, 261 μmol), sodium tert-butoxide (335 mg, 3483 μmol) and tris(dibenzylideneacetone)dipalladium (o) (112 mg, 122 μmol) in one portion. The reaction was heated to reflux for 2 h. After this time TLC and LC/MS show desired product. The reaction was cooled to rt and evaporated in vacuo. The residue was taken up in EtOAc (80 mL) and washed with satd aq. sodium bicarbonate solution (40 mL) and brine (40 mL). The separated organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 1:2) gave desired product.
