Sodium Carbonate → HCID 67021267, Verbindung

HRID 1660972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660972
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19](Br)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].B(O)O>C1(C)C=CC=CC=1.CCO.CCO.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:28]4[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2]

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 201262(4-Methoxyphenyl)boronic acidHCID 67021635[4-(5-Bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 67021267HCID 67021267, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of [4-(5-bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester (0.300 g, 0.84 mmol), 4-methoxyphenylboronic acid (0.152 g, 1.00 mmol, 1.2 equiv), PdCl2(dppf) (18 mg, 0.025 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 1.7 mL, 3.34 mmol, 4 equiv) in toluene/EtOH (12 mL; 5:1, v/v) is stirred and refluxed for 2 h. After further addition of boronic acid (0.100 g, 0.66 mmol) in EtOH (1 mL), the reaction mixture is stirred and refluxed for 30 min, allowed to cool to rt, diluted with EtOAc and H2O, and filtered through a pad of Celite. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel column chromatography purification (Hexane/EtOAc, 3:1) provides the title compound as a yellow solid: ES-MS: 387.1 [M+H]+; single peak at tR=4.27 min (System 1); Rf=0.24 (Hexane/EtOAc, 3:1).

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. stirringthe reaction mixture is stirred
  3. temperaturerefluxed for 30 min
  4. filtrationfiltered through a pad of Celite
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with EtOAc
  7. washThe combined organic phase is washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customSilica gel column chromatography purification (Hexane/EtOAc, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-219dc7064d8642329f035cb0067ebc95
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030311B2

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