Sulfuric Acid → 8-chloro-5-((E)-2-(5-(trifluoromethyl)pyridin-3-yl)vinyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

HRID 1400376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400376
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=3)O)[C:6]3[CH2:24][CH2:25][N:26]([CH3:28])[CH2:27][C:5]=3[C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[OH-].[K+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[CH:12]/[C:14]3[CH:15]=[N:16][CH:17]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:19]=3)[C:6]3[CH2:24][CH2:25][N:26]([CH3:28])[CH2:27][C:5]=3[C:4]=2[CH:3]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 578762152-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-(5-(trifluoromethyl) pyridin-3-yl)ethanol

Produkt 1

HCID 594549398-chloro-5-((E)-2-(5-(trifluoromethyl)pyridin-3-yl)vinyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

2-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-1-(5-(trifluoromethyl)pyridin-3-yl)ethanol (1 equiv.) is refluxed with 25% sulfuric acid for 2 h. The reaction mixture is cooled to 5° C. with an ice-water bath. KOH (15% aq. solution) is added dropwise to the reaction mixture until pH 9-10 is achieved. The reaction mixture is extracted with EtOAc. The combined organic layers are washed with water followed by brine, dried over sodium sulfate and evaporated under vacuum. The crude product is purified by column chromatography over silica gel (100-200 mesh) using a gradient of MeOH-EtOAc (0-10%).

Aufarbeitung

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washThe combined organic layers are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude product is purified by column chromatography over silica gel (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-49fd64dbeb7843bfa497d7d1068e35ca
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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