Morpholine → HCID 11688386, compound

Participants

Reaction Steps

A solution of trifluoromethanesulfonic acid 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester (200 mg, 0.518 mmol), morpholine (0.05 mL, 0.622 mmol), tris(dibenzylideneacetone)dipalladium(0) (9.4 mg, 0.010 mmol), racemic-2,2′bis(diphenylphosphino)-1,1′-binapthyl (19 mg, 0.030 mmol), and cesium carbonate (236 mg, 0.725 mmol) in toluene (5 mL) was heated to reflux for 24 h. The mixture was allowed to cool to room temperature, filtered through a ¾″ silica gel (60 Å) plug, then the plug was washed with EtOAc (40 mL). The resulting solution was concentrated under vacuum and purified via Biotage chromatography with gradient elution from 15% EtOAc/hexanes to 50% EtOAc/hexanes to yield 37 mg (22%) of 5-hydroxy-7-morpholin-4-yl-2-phenyl-chromen-4-one. See, A. Echavarren et al., J. Am. Chem. Soc., 109, pp. 5478-5486 (1987). Rf=0.12 (25% EtOAc/hexanes).

Provenance & Evidence