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HCID 67260634, Verbindung → HCID 178510668, Verbindung

HRID 2359052
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2359052
Br[C:2]1[N:6](CC2C=CC(OC)=CC=2)[N:5]=[C:4]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:3]=1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.Br[C:29]1C(C2C=CN=CC=2)=C(C2SC(Cl)=CC=2)N(CC2C=CC(OC)=CC=2)[N:30]=1>CN(C)C=O.O.C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:18]1[S:17][C:16]([C:4]2[C:3]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)=[C:2]([C:29]#[N:30])[NH:6][N:5]=2)=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 2

HCID 67260634HCID 67260634, VerbindungHCID 67261945HCID 67261945, Verbindung

Produkt 1

HCID 178510668HCID 178510668, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To 4-[5-bromo-3-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine and 4-[3-bromo-5-(5-chloro-2-thienyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine (mixture of isomers 2:1, 1 eq, 0.435 mmol) in 1 mL of N,N-dimethylformamide, were added zinc cyanide (0.65 mmol) and Tetrakis(triphenylphosphine)palladium(0) (0.09 mmol). The mixture was stirred for 5 mins at 160° C. in the microwave. After cooling to room temperature, the reaction mixture was diluted with water and ethyl acetate was added. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was dissolved in 1 mL of trifluoroacetic acid and stirred at 65° C. for 2 h. Water and ethyl acetate were added. And the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with a saturated solution of sodium hydrogen carbonate, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane/methanol 20:1 to 10:1) to afford 19 mg of 3-(5-chloro-2-thienyl)-4-(pyridin-4-yl)-1H-pyrazole-5-carbonitrile (15% yield).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 1 mL of trifluoroacetic acid
  8. stirringstirred at 65° C. for 2 h
  9. additionWater and ethyl acetate were added
  10. extractionAnd the aqueous layer was extracted with ethyl acetate
  11. washThe combined organic extracts were washed with a saturated solution of sodium hydrogen carbonate
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol 20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-9bfa95ee76a742ffbf4fb36da4001a09
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08685974B2

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