Diisopropylethylamine → ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate

HRID 1943621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943621
FC(F)(F)C(O)=O.[NH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].ClC(Cl)(Cl)[C:19]([C:21]1[NH:22][CH:23]=[C:24]([I:26])[CH:25]=1)=[O:20].C(N(CC)C(C)C)(C)C>ClCCl>[I:26][C:24]1[CH:25]=[C:21]([C:19]([NH:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:20])[NH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 116816022,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-oneHCID 72699081ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

Produkt 1

HCID 86658329ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoateAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl (2E)-4-aminobut-2-enoate trifluoroacetate (IV) (0.97 g, 4 mmol) was added to a solution of 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethanone (IX) (0.68 g, 2 mmol) and N,N-diisopropylethylamine (DIPEA) (2.7 mL, 16 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain compound ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate (X, where R1=OCH2CH3) as an off-white solid (0.48 g, 68% yield).

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c1ed7253d4649e1b73d640e6e74305b
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394802B2

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