8-Hydroxyquinoline → HCID 178512036, Verbindung

HRID 499800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499800
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/2=[N:14]\[C:15]#[N:16])=[CH:4][CH:3]=1.[Cl:17][C:18]1[S:22][C:21]([C:23]([NH:25][CH2:26][C:27]2[N:28]=[CH:29][NH:30][CH:31]=2)=[O:24])=[CH:20][CH:19]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:17][C:18]1[S:22][C:21]([C:23]([NH:25][CH2:26][C:27]2[N:28]=[CH:29][N:30]([C:2]3[CH:7]=[CH:6][C:5]([N:8]4[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/4=[N:14]\[C:15]#[N:16])=[CH:4][CH:3]=3)[CH:31]=2)=[O:24])=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 178512035HCID 178512035, VerbindungHCID 178523075HCID 178523075, Verbindung

Produkt 1

HCID 178512036HCID 178512036, VerbindungAusbeute 29,5 %

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 (E)-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)cyanamide (25 mg, 0.078 mmol), 5-Chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (65 mg, 0.18 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (75 mg, 0.54 mmol) in DMSO (1 mL) was degassed with Ar before being charged with CuI (15 mg, 0.079 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the titled compound (10 mg). MS 435.1 and 437.0 (M+H, Cl pattern).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9f8ee12235a744149a435a2f7e072828
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767697B2

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