Citric Acid → HCID 68959366, compound

HRID 2191813Notes

Reaction equation

HRID 2191813 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:33]1[CH:34]=[CH:35][C:36]2[S:40][CH:39]=[CH:38][C:37]=2[CH:41]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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(OCC)(=O)C.C1(C)C=CC=CC=1>[S:40]1[C:36]2[CH:35]=[CH:34][C:33]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:41][C:37]=2[CH:38]=[CH:39]1

Participants

10

Reactant 5

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 27765785-Bromo-1-benzothiopheneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 68959354HCID 68959354, compound

Product 1

HCID 68959366HCID 68959366, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-(4-(methanesulfonamido)phenyl)benzoate 0.12 g and cesium carbonate 0.27 g were added 5-bromobenzothiophene 0.14 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.9 mg, tris(dibenzylideneacetone)dipalladium(0) 3.0 mg and palladium acetate 1.5 mg at room temperature, and it was stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=2:1] to give tert-butyl 2-((benzothiophen-5-yl)amino)-4-(4-(methanesulfonamido)phenyl)benzoate.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationwas filtrated
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7612fd0d10e445029da1df02f16d5696
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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