Potassium Acetate → HCID 178459390, Verbindung

HRID 521204

Reaktionsgleichung

Reaktionsgleichung von HRID 521204
C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C([O-])(=O)C.[K+].[NH2:40][C:41]1[C:45]([C:46]([NH2:48])=[O:47])=[CH:44][NH:43][N:42]=1.Br[C:50]1[CH:61]=[CH:60][C:53]([C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55])=[CH:52][CH:51]=1>CCOC(C)=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].CC(O)C>[C:46]([C:45]1[C:41]([NH:40][C:50]2[CH:61]=[CH:60][C:53]([C:54]([O:56][CH:57]([CH3:58])[CH3:59])=[O:55])=[CH:52][CH:51]=2)=[N:42][NH:43][CH:44]=1)(=[O:47])[NH2:48]

Komponenten

8

Edukt 4

HCID 517044Potassium AcetateHCID 603913Isopropyl 4-bromobenzoateHCID 11953610Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneHCID 178513763HCID 178513763, Verbindung

Produkt 1

HCID 178459390HCID 178459390, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A round-bottomed flask was charged with 2-propanol (595 mL), and nitrogen was bubbled through the 2-propanol for 2 hours. Pd2(dba)3 (1.63 g, 1.78 mmol) and di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethylbiphenyl-2-yl)phosphine (3.43 g, 7.14 mmol) were added, and the mixture was stirred for 20 minutes. Potassium acetate (17.5 g, 178 mmol), 3-amino-1H-pyrazole-4-carboxamide (15.0 g, 119 mmol), and isopropyl 4-bromobenzoate (34.7 g, 143 mmol) were then added, and the reaction mixture was heated to 75° C. for 6.5 hours. The reaction mixture was then cooled to 23° C., diluted with EtOAc (500 mL), and filtered through celite. The filtrate was adsorbed onto silica gel in vacuo and purified by MPLC on silica gel (using a gradient elution of 30-90%, EtOAc/hexanes) to afford the title compound.

Aufarbeitung

  1. customwas bubbled through the 2-propanol for 2 hours
  2. temperatureThe reaction mixture was then cooled to 23° C.
  3. filtrationfiltered through celite
  4. custompurified by MPLC on silica gel (
  5. washa gradient elution of 30-90%, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d31c3e5b25124af080468c855828aabe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328099B2

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