Morpholine → HCID 11688386, compound

HRID 884453Notes

Reaction equation

HRID 884453 reaction equation
[OH:1][C:2]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[CH:5]=[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:7]2.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:1][C:2]1[CH:11]=[C:10]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[CH:5]=[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:7]2

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 11090323HCID 11090323, compound

Product 1

HCID 11688386HCID 11688386, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

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).

Workup

  1. temperatureto reflux for 24 h
  2. filtrationfiltered through a ¾″ silica gel (60 Å) plug
  3. washthe plug was washed with EtOAc (40 mL)
  4. concentrationThe resulting solution was concentrated under vacuum
  5. custompurified via Biotage chromatography with gradient elution from 15% EtOAc/hexanes to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-f7a2caff891a4c8280a22af89a1c1598
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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