Cesium carbonate → 7-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

HRID 14474

Reaction equation

HRID 14474 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:27]([CH3:29])[CH3:28])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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:82](=[NH:95])([C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:82](=[N:95][C:13]1[CH:12]=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:9]([CH:27]([CH3:29])[CH3:28])[O:10]2)=[CH:15][CH:14]=1)([C:89]1[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=1)[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 86625612Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester

Product 1

HCID 866256137-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester (6.96 g, 15.6 mmol), palladium acetate (0.35 g, 1.56 mmol), cesium carbonate (12.7 g, 38.9 mmol) and racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 0.97 g, 1.56 mmol) in anhydrous tetrahydrofuran (230 ml) under an atmosphere of nitrogen is treated with benzophenone imine (3.66 g, 20.2 mmol) and allowed to stir at 80° C. for 22 hours. After allowing the resultant mixture to stir at room temperature for an additional 24 hours, it is diluted with water (300 ml) and extracted with ethyl acetate (3×300 ml). The organic extracts are combined, washed with brine, dried (MgSO4), filtered, concentrated in vacuo and purified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane) to afford the desired compound as a dark yellow solid.

Workup

  1. stirringto stir at room temperature for an additional 24 hours
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-0479cbb4c10b496d83215aa7d8ce704d
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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