HCID 12628585, Verbindung → Ethyl 3-methyl-1H-indole-5-carboxylate

HRID 1356721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1356721
Br[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][CH:6]=[CH2:7]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:10]1[CH:11]=[C:2]2[C:3](=[CH:8][CH:9]=1)[NH:4][CH:5]=[C:6]2[CH3:7])([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 1

HCID 12628585HCID 12628585, Verbindung

Produkt 1

HCID 12628587Ethyl 3-methyl-1H-indole-5-carboxylateAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-bromo-4-carboethoxy-N-allylaniline (J. Org. Chem., 45, 2710 (1980)) (650 mg, 2.29 mmol) in acetonitrile (10 ml), tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), palladium (II) acetate (25.7 mg, 0.114 mmol) and TEA (0.413 ml, 2.98 mmol) were added and stirred overnight in a sealed tube at 100° C. After filtering the reaction mixture, the filtrate was evaporated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:2) to give the titled compound (340 mg, 73%).

Aufarbeitung

  1. filtrationAfter filtering the reaction mixture
  2. customthe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-222068574c3146c29a34528ae0c00e15
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586630B1

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