Morpholine → HCID 54223004, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a mixture of methyl4-(trifluoromethylsulfonyloxy)phenyl acetate (1.0 g, 3.35 mmol), cesium carbonate (1.6 g, 4.69 mmol), palladium (II) acetate (22 mg, 0.10 mmol), (S)-BINAP (93 mg, 0.15 mmol), and morpholine (0.35 mL, 4.02 mmol) in 8 mL toluene and the reaction mixture was heated to 80° C. for 6 hours. The reaction was then cooled, celite was added, and the mixture was concentrated. Chromatography was performed on a Biotage flash 40i chromatography module by loading the dried celite into a SIM and eluting with 20% ethyl acetate/hexanes (40S cartridge) providing 250 mg (37%) of the title compound as a yellow oil. 1H NMR (CDCl3; 300 MHz) δ7.19 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.3 Hz, 2H), 3.89-3.85 (m, 4H), 3.69 (s, 3H), 3.56 (s, 2H), 3.17-3.13 (m, 4H).

Provenance & Evidence