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Potassium Iodide → 10-bromo-2-i-propoxycarbonylmethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850766
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850766
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29].[I-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[C:8]4[CH:9]=[C:10]([O:15][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Produkt 1

HCID 1936491110-bromo-2-i-propoxycarbonylmethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-oneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one (3 g) obtained in Example 59 was suspended in dimethyl sulfoxide (120 ml), and potassium carbonate (2.6 g) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and i-propyl bromoacetate (1.4 ml) and potassium iodide (1 grain) were added in succession to the mixture. The mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into ice water (500 ml), and the crystals precipitated were recovered by filtration. The crude crystals were purified by silica gel flash column chromatography (eluent: methylene chloride containing 1% methanol) to obtain the title compound (2.0 g, 51%).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customthe crystals precipitated
  3. filtrationwere recovered by filtration
  4. customThe crude crystals were purified by silica gel flash column chromatography (eluent: methylene chloride containing 1% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-29ce2678844b4085ae179ee64ebefe80
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06018046

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