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

HRID 49920

Reaktionsgleichung

Reaktionsgleichung von HRID 49920
[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]([NH:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27])(=[O:23])[CH3:22].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([NH:24][C:25](=[CH:30][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:26]([O:28][CH3:29])=[O:27])(=[O:23])[CH3:22]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 11111864t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate

Produkt 1

HCID 68833044Methyl 2-Acetamido-3-[2-(2-(t-butoxycarbonylamino)ethoxy)-4-cyanophenyl]acrylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

18.0 g (46.4 mmol) of 3-[2-(t-butoxycarbonylamino)ethoxy]-4-iodobenzonitrile was dissolved in 200 ml of dimethylformamide (DMF). 13.3 g (92.8 mmol) of methyl 2-acetamidoacrylate, 2.82 g (9.28 mmol) of tris(2-methylphenyl)phosphine, 1.04 g (4.64 mmol) of palladium (II) acetate and 12.9 ml (92.8 mmol) of triethylamine were added to the obtained solution, and they were stirred at 115° C. for 4 hours. The solvent was evaporated to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customto obtain the crude product, which
  3. customwas purified by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-046281170f08469dba7a019a60a28e30
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710056B2

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