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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1043083Erstellt: 25. Oktober 2026

Triethylamine → (Z)-tert-butyl 5-(benzyloxy)-3-(3-morpholino-3-oxoprop-1-enyl)-1H-indole-1-carboxylate

https://huagongshe.com/reaction/1043083

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
EduktTri-o-tolylphosphineHCID 80271—
EduktAcryloylmorpholineHCID 98723—
Edukt5-(Benzyloxy)-3-bromo-1H-indole, N-BOC protectedHCID 40428554—
Katalysatorpalladium(II) acetateHCID 167845—
LösungsmittelDimethylformamideHCID 6228—
LösungsmittelEthyl AcetateHCID 8857—
LösungsmittelAmmonium ChlorideHCID 25517—
Produkt(Z)-tert-butyl 5-(benzyloxy)-3-(3-morpholino-3-oxoprop-1-enyl)-1H-indole-1-carboxylateHCID 67227351—

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A mixture of tert-butyl 5-(benzyloxy)-3-bromo-1H-indole-1-carboxylate (2.011 g), 1-morpholinoprop-2-en-1-one (0.776 g), palladium acetate (31 mg), tri-o-tolylphosphine (187 mg) and triethylamine (1.14 mL) in N,N-dimethylformamide (14 mL) under nitrogen atmosphere was stirred at 100° C. overnight. The mixture was diluted with ethyl acetate and saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (80% ethyl acetate-hexane) to give the desired product.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08557983B2
Quelldatensatzuspto-grants-2013_10
ORD IDord-26e8b1350a8a42aba2a4798eedc00efe
Quellennotizuspto-grants-2013_10