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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 58635Erstellt: 25. Oktober 2026

Sodium Carbonate → 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

https://huagongshe.com/reaction/58635

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium CarbonateHCID 10340—
EduktLithium ChlorideHCID 433294—
Edukt4-(Triethylsilyl)-3-butyn-1-olHCID 2760694—
Edukt4-Amino-3-iodobenzonitrileHCID 4416395—
KatalysatorPalladium ChlorideHCID 24290—
KatalysatorFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
LösungsmittelDimethylformamideHCID 6228—
Produkt3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrileHCID 6683213351,8%

Reaktionsschritte

4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 mL; 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 mL) was stirred at 100° C. for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09434722B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-852fc4767c60491383d952da2fa0d845
Quellennotizuspto-grants-2016_09