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

HRID 884455Notes

Reaction equation

HRID 884455 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7](OS(C(F)(F)F)(=O)=O)=[CH:8][C:9]=2[OH:13])[O:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:8][C:9]=2[OH:13])[O:4][C:3]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 58805196trifluoromethanesulfonic acid 3,5-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl ester

Product 1

HCID 588051983,5-Dihydroxy-7-morpholin-4-yl-2-phenyl-chromen-4-oneYield 9.2%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

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. Rf=0.22 (100% CH2Cl2).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a ½″ silica gel (60 Å) plug
  3. washThe plug was washed with EtOAc (40 mL)
  4. concentrationthe filtrate concentrated
  5. customThe concentrate was purified via Biotage chromatography
  6. washeluting with 100% CH2Cl2

Sources & evidence

ORD record
ord-46bf7c5265bb415289afcbdabf8506f3
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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