HCID 178418260, Verbindung → HCID 178440448, Verbindung

HRID 33236

Reaktionsgleichung

Reaktionsgleichung von HRID 33236
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1I)=[O:5])[CH3:2].[Cu](C#N)[C:16]#[N:17]>[C-]#N.C([N+](CC)(CC)CC)C.CN(C=O)C.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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH2:12][CH2:13][CH3:14])[C:10]=1[C:16]#[N:17])=[O:5])[CH3:2]

Komponenten

7

Edukt 2

HCID 178418260HCID 178418260, VerbindungHCID 178440449HCID 178440449, Verbindung

Produkt 1

HCID 178440448HCID 178440448, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 3014735Tetraethylammonium cyanideKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

1.5 g (4.9 mmol) of 4-Iodo-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester, 0.87 g (9.7 mmol) of copper cyanide and 404 mg (2.4 mmol) of tetraethylammonium cyanide were dissolved in 10 ml of DMF and 20 ml of tetrahydrofuran and the solution was degassed with argon. 223 mg (0.2 mmol) of Tris(dibenzylideneacetone)dipalladium (0) and 404 mg (0.7 mmol) of 1,1′-bis-(diphenylphosphino) ferrocene were added at RT. The reaction was stirred at 120° C. for 5 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and this solution was washed with saturated aqueous sodium bicarbonate. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography eluting with n-heptane:ethyl acetate/ 1:1.

Aufarbeitung

  1. custom20 ml of tetrahydrofuran and the solution was degassed with argon
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthis solution was washed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by silica gel chromatography
  9. washeluting with n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-19b839865e974f4484444f89029ab1c4
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429581B2

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