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Trimethylsilylacetylene → 2-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374920
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1374920
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C(N(CC)CC)C.C(OCC)C.[Cu]Cl>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1)([CH3:24])[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 66111Trimethylsilylacetylene2×HCID 21078374HCID 21078374, Verbindung

Produkt 1

HCID 210784012-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 62652Cuprous chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel
HCID 8471
Triethylamine
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-(5-Bromo-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide (0.40 g), trimethylsilylacetylene (0.24 ml), copper (I) chloride (0.015 g) and palladium dichloride bis(triphenyl)phosphine (0.030 g) in dry triethylamine (4 ml) were sealed in a glass tube and heated to 90° C. for 3 hours. The mixture was cooled to ambient temperature and stored for 18 hours. Further trimethylsilylacetylene (0.24 ml) and palladium dichloride bis(triphenyl)-phosphine (0.030 g) were added and the mixture re-heated in the sealed tube for another 5.5 hours. The reaction mixture was cooled to ambient temperature, stored for 72 hours, diluted with diethyl ether and washed with water (three times). The organic phase was separated, dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow gum, ca. 0.4 g, containing the required product, which was used in the next Stage without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture re-heated in the sealed tube for another 5.5 hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. waitstored for 72 hours
  5. washwashed with water (three times)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a dark yellow gum, ca. 0.4 g

Quellen und Nachweise

ORD-Eintrag
ord-40abed4075dd486d9538de71bf5d5e8f
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07166621B2

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