Cesium carbonate → HCID 66990551, compound

HRID 454608Notes

Reaction equation

HRID 454608 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[CH2:48]([O:55][C:56]1[CH:83]=[C:82](I)[CH:81]=[CH:80][C:57]=1[C:58]([NH:60][C:61]1[CH:73]=[C:72]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH:71]=[CH:70][C:62]=1[C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])=[O:59])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl.O.C1(C)C=CC=CC=1>[CH2:48]([O:55][C:56]1[CH:83]=[C:82]([N:5]([CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[CH3:6])[CH:81]=[CH:80][C:57]=1[C:58]([NH:60][C:61]1[CH:73]=[C:72]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH:71]=[CH:70][C:62]=1[C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])=[O:59])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

10

Reactant 4

HCID 10796Cesium carbonate2×HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-2×HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl2×HCID 66990554HCID 66990554, compound

Product 1

HCID 66990551HCID 66990551, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 962WaterSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

N,N,N′-Trimethylethylenediamine (0.12 mL), cesium carbonate (0.35 g), tris(dibenzylideneacetone)dipalladium(0) (3.3 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8.6 mg), and palladium(II) acetate (1.6 mg) were added to a toluene (3.0 mL) suspension of tert-butyl 2-(2-(benzyloxy)-4-iodobenzamido)-4-phenylbenzoate (0.22 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours and 10 minutes. The reaction mixture was cooled to room temperature, and then N,N,N′-trimethylethylenediamine (0.12 mL), cesium carbonate (0.35 g), tris(dibenzylideneacetone)dipalladium(0) (3.3 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8.6 mg), and palladium(II) acetate (1.6 mg) were added to the reaction mixture, followed by heating to reflux under a nitrogen atmosphere for 8 hours. The reaction mixture was cooled to room temperature, and then water and chloroform were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-93% chloroform/methanol] to obtain 0.072 g of tert-butyl 2-(2-(benzyloxy)-4-((2-(dimethylamino)ethyl)(methyl)amino)benzamido)-4-phenylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 4 hours and 10 minutes
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 8 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe insoluble substance was removed by filtration
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-93% chloroform/methanol]

Sources & evidence

ORD record
ord-a1a9b4ceeb574dd9aa372e5c68f18393
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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