8-Hydroxyquinoline → HCID 24760755, Verbindung

HRID 499790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499790
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[S:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[S:20][C:19]([C:21]([NH:23][CH2:24][C:25]2[N:26]=[CH:27][NH:28][CH:29]=2)=[O:22])=[CH:18][CH:17]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:15][C:16]1[S:20][C:19]([C:21]([NH:23][CH2:24][C:25]2[N:26]=[CH:27][N:28]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]4=[S:14])=[CH:4][CH:3]=3)[CH:29]=2)=[O:22])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 86616333HCID 86616333, VerbindungHCID 178523075HCID 178523075, Verbindung

Produkt 1

HCID 24760755HCID 24760755, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 1-(4-iodophenyl)pyridine-2(1H)-thione prepared above (65 mg, 0.21 mmol), 5-chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 prepared in Example 11 (65 mg, 0.18 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (75 mg, 0.54 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (27 mg, 0.14 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (15 mg). MS 427.0 and 429.0 (M+H, Cl pattern).

Aufarbeitung

  1. customwas degassed with Ar
  2. customIt was then purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-041ab02406ff4adea4886397c2d48b4f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767697B2

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