Morpholine → 3,5-Dihydroxy-7-morpholin-4-yl-2-phenyl-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

A solution of trifluoromethanesulfonic acid 3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester (90 mg, 0.224 mmol), morpholine (0.024 mL, 0.269 mmol), tris(dibenzylideneacetone) dipalladium(0) (10 mg, 0.011 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (13 mg, 0.045 mmol), and K3PO4 (67 mg, 0.314 mmol) in THF (1.2 mL) was capped and heated to 85° C. After 9 h, the reaction mixture was allowed to cool to room temperature, then filtered through a ½″ silica gel (60 Å) plug. The plug was washed with EtOAc (40 mL) and the filtrate concentrated. The concentrate was purified via Biotage chromatography eluting with 100% CH2Cl2 to yield 7 mg (9%) of 3,5-dihydroxy-7-morpholin-4-yl-2-phenyl-chromen-4-one.

Provenance & Evidence