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Dimethylacetamide → HCID 89700014, Verbindung

HRID 1055753
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1055753
[C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[C:33](Cl)[N:34]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.[CH3:65][N:66](C)C(=O)C>C(OCC)(=O)C.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.[Zn].[C-]#N.[Zn+2].[C-]#N>[C:1]([C:5]1[CH:6]=[C:7]([CH:32]=[C:33]([C:65]#[N:66])[N:34]=1)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)[CH:12]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 31374DimethylacetamideHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 89699945HCID 89699945, Verbindung

Produkt 1

HCID 89700014HCID 89700014, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 23994
Zinc
Katalysator
HCID 2733347Palladium(II) trifluoroacetateKatalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Under argon, a mixture of 137 mg (0.28 mmol) of the compound of Example 65, 4.04 mg (0.012 mmol) of palladium(II) trifluoroacetate, 9.91 mg (0.025 mmol) of racemic 2-di-tert-butylphosphino-1,1′-binaphthyl, 3.51 mg (0.054 mmol) of zinc flakes and 18.6 mg (0.16 mmol) of zinc cyanide in 1.5 ml N,N-dimethylacetamide was stirred at 95° C. for 20 hours. After cooling, the mixture was diluted with 80 ml of ethyl acetate and the mixture was washed in each case once with 10 ml of water and 10 ml saturated sodium chloride solution. The organic phase was dried over sodium sulphate and, after filtration, concentrated under reduced pressure. The residue obtained in this manner was purified by chromatography on a Biotage system (25 g Snap column; mobile phase gradient ethyl acetate/hexane, starting with 70% ethyl acetate, then increasing rapidly to 100% ethyl acetate). Further purification was by preparative thick-layer chromatography (2 mm layer thickness with concentration zone, mobile phase ethyl acetate, elution with methylene chloride/methanol 7:3). This gave 56 mg (38% of theory) of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe mixture was washed in each case once with 10 ml of water and 10 ml saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. filtrationafter filtration
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained in this manner
  7. customwas purified by chromatography on a Biotage system (25 g Snap column
  8. temperatureincreasing rapidly to 100% ethyl acetate)
  9. customFurther purification
  10. concentrationwas by preparative thick-layer chromatography (2 mm layer thickness with concentration zone, mobile phase ethyl acetate, elution with methylene chloride/methanol 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-e7f88f5b5e144a79b254d62dd1ac8cf0
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09394309B2

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