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Dimethylformamide → HCID 68455479, Verbindung

HRID 2357648
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357648
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.[CH3:23][N:24](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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.C(Cl)(Cl)Cl.[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]>[C:23]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1)#[N:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 6228DimethylformamideHCID 77230175Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

Produkt 1

HCID 68455479HCID 68455479, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator
HCID 11029508
Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (2.49 g, 7.96 mmol) and zinc cyanide (1.87 g, 15.9 mmol) was added DMF (39.8 mL). The mixture was sparged with nitrogen for 15 min, and tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.330 g, 0.318 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.177 g, 0.318 mmol) were added. The reaction was heated to 100° C. for 30 min. The reaction mixture was diluted with 100 mL ethyl acetate, partitioned with sodium bicarbonate (saturated, aqueous), and the organics were washed 3×50 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound. MS (ES+): 304(M+H)+.

Aufarbeitung

  1. customThe mixture was sparged with nitrogen for 15 min
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washthe organics were washed 3×50 mL with sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0c140700ee914f95afbe6dbd4487d259
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759337B2

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