Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → ethyl-3-(4-bromo-6-fluoro-1H-indol-2-yl)prop-2-enoate

HRID 857397Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857397
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:12]=O)[NH:6]2.[CH2:14]([O:16][C:17]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:18])[CH3:15]>C1COCC1>[CH2:14]([O:16][C:17](=[O:18])[CH:19]=[CH:12][C:5]1[NH:6][C:7]2[C:3]([CH:4]=1)=[C:2]([Br:1])[CH:10]=[C:9]([F:11])[CH:8]=2)[CH3:15]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 218674094-bromo-6-fluoro-1H-indole-2-carbaldehyde

Produkt 1

HCID 69561024ethyl-3-(4-bromo-6-fluoro-1H-indol-2-yl)prop-2-enoateAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-6-fluoro-1H-indole-2-carbaldehyde (1.8 g, 7.4 mmol) in THF (100 mL) at r.t. was added (ethoxycarbonylmethylene)triphenylphosphorane (5 g, 14 mmol). The mixture was stirred for 2 hours at r.t. and the mixture was filtered through a silica gel pad eluted with 40% EtOAc and the filtrate was concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc to give 1.6 g of the title compound.

Aufarbeitung

  1. filtrationthe mixture was filtered through a silica gel pad
  2. washeluted with 40% EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluted with 20% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2fcb3fcfa6a94bb2bb711dddfbd600bf
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144913B2

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