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Triphenylphosphine → 1H-Indazole-1-carboxylic acid, 5-methyl-3-[2-(trimethylsilyl)ethynyl]-, 1,1-dimethylethyl ester

HRID 1520003
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1520003
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].[Cu](I)I>[CH3:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:3]=[C:2]2[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 20785165HCID 20785165, Verbindung

Produkt 1

HCID 679810201H-Indazole-1-carboxylic acid, 5-methyl-3-[2-(trimethylsilyl)ethynyl]-, 1,1-dimethylethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysator
HCID 167845
palladium(II) acetate
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a round bottom flask were introduced tert-butyl 3-iodo-5-methyl-1H-indazole-1-carboxylate (8.3 g; 23.2 mmol; 1.0 eq.), (trimethylsilyl)acetylene (6.8 mL; 48.8 mmol; 2.1 eq.), Pd(OAc)2 (521 mg; 2.3 mmol; 0.1 eq.), triphenylphosphine (1.22 g; 4.65 mmol; 0.2 eq.) and copper iodide (442 mg; 2.32 mmol; 0.1 eq.) in TEA (57 mL). The reaction mixture was degassed and stirred at 80° C. under N2 for 1 hour. Et2O was added and the reaction mixture was filtrated through a celite pad. The filtrate was then washed twice with an aqueous saturated solution of NH4Cl and brine, dried over magnesium sulfate, filtered and concentrated. This crude was purified by flash chromatography on silica (Heptane/EtOAc, gradient from 100:0 to 10:90) to afford the title compound as a beige solid.

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. additionEt2O was added
  3. filtrationthe reaction mixture was filtrated through a celite pad
  4. washThe filtrate was then washed twice with an aqueous saturated solution of NH4Cl and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis crude was purified by flash chromatography on silica (Heptane/EtOAc, gradient from 100:0 to 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-585dbd62e0b8415e8585b6d6d05c61d3
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09073892B2

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