Triethylamine → Ethyl 3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]acrylate

HRID 2414402

Reaktionsgleichung

Reaktionsgleichung von HRID 2414402
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1I)[C:15]#[N:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15]#[N:16])[CH:17]=[CH:18][C:19]=1[CH:23]=[CH:22][C:21]([O:25][CH2:26][CH3:27])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 8857Ethyl AcetateHCID 11111864t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate

Produkt 1

HCID 69921285Ethyl 3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]acrylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

11.0 g (28.4 mmol) of 3-[2-(t-butoxycarbonylamino)ethoxy]-4-iodobenzonitrile was dissolved in 200 ml of DMF. 15.4 ml (142 mmol) of ethyl acrylate, 20 ml (142 mmol) of triethylamine and 127 mg (0.567 mmol) of palladium acetate were added to the obtained solution. They were stirred at 100° C. overnight and then treated with ethyl acetate as the extraction solvent in an ordinary manner to obtain the crude product. After the purification by the silica gel column chromatography, the title compound was obtained.

Aufarbeitung

  1. customto obtain the crude product
  2. customAfter the purification by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6fcd5222fd0b47fe8a222238ed191871
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06812231B2

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