Cesium carbonate → Tert-butyl 2-((benzothiophen-5-yl)amino)-4-(indolin-1-yl)benzoate

HRID 2191827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191827
[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].Br[C:25]1[CH:26]=[CH:27][C:28]2[S:32][CH:31]=[CH:30][C:29]=2[CH:33]=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.C1(C)C=CC=CC=1>[S:32]1[C:28]2[CH:27]=[CH:26][C:25]([NH:1][C:2]3[CH:14]=[C:13]([N:15]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH2:17][CH2:16]4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:33][C:29]=2[CH:30]=[CH:31]1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonate2×HCID 27765785-Bromo-1-benzothiophene2×HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3×HCID 68957351HCID 68957351, Verbindung

Produkt 1

HCID 68960417Tert-butyl 2-((benzothiophen-5-yl)amino)-4-(indolin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysator3×HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator3×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To toluene 3.0 mL solution of tert-butyl 2-amino-4-(indolin-1-yl)benzoate 0.12 g were added 5-bromobenzothiophene 0.21 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 110° 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 110° C. for 6 hours. 5-Bromobenzothiophene 0.21 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 were added at room temperature, and it was stirred at 110° 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 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-((benzothiophen-5-yl)amino)-4-(indolin-1-yl)benzoate.

Aufarbeitung

  1. stirringwas stirred at 110° C. for 6 hours
  2. stirringit was stirred at 110° 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. customcollected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washing with saturated sodium chloride aqueous solution
  10. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0ef6b1f25a145bf8ab1fc4d29948d28
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08327467B2

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