Acetonitrile → 1-ethyl-5-(2-hydroxy-2-methylpropyl)-4-(3-trimethylsilylprop-1-ynyl) 1H-pyrazole-3-carbonitrile

HRID 1984502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984502
[CH2:1]([N:3]1[C:7]([CH2:8][C:9]([OH:12])([CH3:11])[CH3:10])=[C:6](I)[C:5]([C:14]#[N:15])=[N:4]1)[CH3:2].[CH2:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[C:17]#[CH:18].C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:3]1[C:7]([CH2:8][C:9]([OH:12])([CH3:11])[CH3:10])=[C:6]([C:18]#[C:17][CH2:16][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]([C:14]#[N:15])=[N:4]1)[CH3:2]

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 83378Trimethyl-2-propynylsilaneHCID 669585891-ethyl-5-(2-hydroxy-2-methylpropyl)4-iodo-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 669587061-ethyl-5-(2-hydroxy-2-methylpropyl)-4-(3-trimethylsilylprop-1-ynyl) 1H-pyrazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 1-ethyl-5-(2-hydroxy-2-methylpropyl)4-iodo-1H-pyrazole-3-carbonitrile (900 mg, 2.81 mmol), propargyltrimethylsilane (0.8 mL, 5.6 mmol), copper(I) iodide (107 mg, 0.562 mmol), dichlorobis(triphenylphosphine)palladium(II) (197 mg, 0.281 mmol), triethylamine (1.2 mL, 8.4 mmol) and acetonitrile (14 mL) were combined and then heated at reflux for five hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, and then filtered through a layer of silica gel. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge, eluting with a gradient of 0 to 80% ethyl acetate in hexanes) to provide 1-ethyl-5-(2-hydroxy-2-methylpropyl)4-(3-trimethylsilylprop-1-ynyl)-1H-pyrazole-3-carbonitrile as a yellow oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for five hours
  3. filtrationfiltered through a layer of silica gel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a HORIZON HPFC system (40+M cartridge
  6. washeluting with a gradient of 0 to 80% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7a30b72af59345eeb236d05f213d68ef
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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