Pyrazole → 1-(naphthalen-1-yl)-1H-pyrazole

HRID 386381

Reaktionsgleichung

Reaktionsgleichung von HRID 386381
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.I[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[C:15]1([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 1048PyrazoleHCID 70041-IodonaphthaleneHCID 10796Cesium carbonate

Produkt 1

HCID 6473051-(naphthalen-1-yl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1H-pyrazole (300 mg, 4.4 mmol), iodonaphthalene (1.1 g, 4.4 mmol), copper (I) iodide (126 mg, 0.66 mmol), Cs2CO3 (2.15 g, 6.6 mmol) in DMF (5 mL) was evacuated and filled with nitrogen twice. The reaction was then stirred at room temperature for 30 minutes and then at 120° C. for 2 days. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, filtered through silica gel and concentrated to give 1-(naphthalen-1-yl)-1H-pyrazole as pure solid. (800 mg, 93%).

Aufarbeitung

  1. customwas evacuated
  2. additionfilled with nitrogen twice
  3. waitat 120° C. for 2 days
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through silica gel
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd1102cf020049879ce49d89a44449ac
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372807B2

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