Trimethylsilylacetylene → 2,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamide

HRID 1160003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160003
Br[C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>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.C1COCC1>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:3]=[CH:4][C:5]=1[O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 22636844N-[5-bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide

Produkt 1

HCID 595114262,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamideAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To an oven-dried flask under N2 was added N-[5-bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide (1.53 g, 0.005 mol), anhydrous degassed THF (100 mL), dichlorobis(triphenylphosphine)palladium(II) (0.45 g, 0.0006 mol), Cu(I)I (73 mg, 0.38 mmol), and trimethylsilylacetylene (1.26 g, 0.013 mol). Next, TEA (5.19 g, 0.05 mol) was added dropwise and the resulting mixture was heated at 60° C. overnight. The crude reaction mixture was adsorbed to silica gel and purified by column chromatography (0-10% EtOAc in hexanes) to afford the desired product (0.68 g, 42%) as an off white solid. ESIMS (M−H)−=314.

Aufarbeitung

  1. customThe crude reaction mixture
  2. custompurified by column chromatography (0-10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-581112a9c3a046d39a63cf2e42f65cd1
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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