Cesium carbonate → HCID 68958040, compound

HRID 2191825Notes

Reaction equation

HRID 2191825 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16]2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].I[C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1.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>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.CC(O)(C)C>[OH:31][C:27]1[CH:26]=[C:25]([NH:1][C:2]2[CH:14]=[C:13]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH:12]=[CH:11][C:3]=2[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonate2×HCID 122723-IodophenolHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3×HCID 68957351Tert-butyl 2-amino-4-(indolin-1-yl)benzoate

Product 1

HCID 68958040HCID 68958040, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst3×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst3×HCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To 2-methyl-2-propanol 3.0 mL solution of tert-butyl 2-amino-4-(indolin-1-yl)benzoate 0.12 g were added 3-iodophenol 0.22 g, cesium carbonate 0.26 g, tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg at room temperature, and it was stirred at 70° C. for 12 hours. Tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg were added to it, and it was stirred at 70° C. for 7 hours. Cesium carbonate 0.26 g, tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg were added to it, and it was stirred at 70° C. for 12 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2,008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 2-((3-hydroxyphenyl)amino)-4-(indolin-1-yl)benzoate.

Workup

  1. stirringwas stirred at 70° C. for 7 hours
  2. stirringwas stirred at 70° C. for 12 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationinsoluble matter was filtrated
  5. additionethyl acetate and 10% citric acid aqueous solution were added to it
  6. customThe organic layer was separated
  7. washafter washing with saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-93183e960e3c458c885fe575d34a27ce
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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