Cesium carbonate → Methyl 5-cyano-4-[2-(diphenylmethylene)hydrazino]-2-furoate

HRID 1723929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723929
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[O:11][C:12]=1[C:13]#[N:14].[C:19](=[N:32][NH2:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O=[Si]=O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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.[Fe+2]>[C:13]([C:12]1[O:11][C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:8]=1[NH:33][N:32]=[C:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[N:14]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 24261SilicaHCID 79304DiphenylmethylidenehydrazineHCID 68828530Methyl 4-bromo-5-cyanofuran-2-carboxylate

Produkt 1

HCID 86606584Methyl 5-cyano-4-[2-(diphenylmethylene)hydrazino]-2-furoateAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
102 °C

Versuchsvorschrift

Palladium acetate (2.098 g; 9.347 mmol), DPPF (10.36 g; 18.69 mmol) and cesium carbonate (85.27 g; 0.262 mmol) were charged in a dry reaction flask under argon. A preformed dry solution of methyl 4-bromo-5-cyano-2-furoate (43.00 g, 0.187 mol) and benzophenone hydrazone (44.02 g, 0.224 mol) in 1.2 L of toluene was transferred via cannula into the reaction flask. The resulting suspension was vigorously stirred at 100-104° C. for 45 hours under argon. The reaction mixture was cooled to about 70° C., added with 65 g of Dicalite® and filtered; the panel was washed twice with hot toluene (400 mL). The filtrate was concentrated under vacuum to a small volume and kept at +4° C. for 18 hours. The solid was collected by filtration and washed with 60 mL of toluene to yield 53.52 g of yellowish product.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to about 70° C.
  2. filtrationfiltered
  3. washthe panel was washed twice with hot toluene (400 mL)
  4. concentrationThe filtrate was concentrated under vacuum to a small volume
  5. waitkept at +4° C. for 18 hours
  6. filtrationThe solid was collected by filtration
  7. washwashed with 60 mL of toluene

Quellen und Nachweise

ORD-Eintrag
ord-c06c0eec393c4d5f97e79d28fc4b6ae9
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485661B2

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