Morpholine → {1-[4-(8-Morpholin-4-yl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

{1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg, 0.091 mmol), morpholine (10 μL, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (5 mg, 0.005 mmol), (S)-BINAP (9 mg, 0.015 mmol) and cesium carbonate (42 mg, 0.127 mmol) were suspended in toluene (1 mL) in a microwave vial. The vial was sealed, evacuated and flushed twice with nitrogen. The reaction mixture was heated in a microwave at 150° C. for 1 h. Further morpholine (10 μL, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (5 mg, 0.005 mmol), (S)-BINAP (9 mg, 0.015 mmol) and cesium carbonate (42 mg, 0.127 mmol) were added to the vial and the resultant mixture was heated in a microwave at 150° C. for 1.5 h. Further morpholine (10 μL, 0.11 mmol), tris(dibenzylideneacetone)dipalladium(0) (5 mg, 0.005 mmol), (S)-BINAP (9 mg, 0.015 mmol) and cesium carbonate (42 mg, 0.127 mmol) were added to the vial and the resultant mixture was heated in a microwave at 150° C. for 1 h. The reaction mixture was diluted with EtOAc, washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 100% ethyl acetate in DCM) to afford the title compound as a pale yellow solid (35 mg, 70%). LCMS (Method G): RT=4.33 min, [M+H]+=553.

Provenance & Evidence