8-Hydroxyquinoline → HCID 178482154, Verbindung

HRID 2357813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357813
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]\[CH3:15])=[CH:4][CH:3]=1.[Cl:16][C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][C:26]2[N:27]=[CH:28][NH:29][CH:30]=2)=[O:23])=[CH:19][CH:18]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:16][C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][C:26]2[N:27]=[CH:28][N:29]([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]\[CH3:15])=[CH:4][CH:3]=3)[CH:30]=2)=[O:23])=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 178482153HCID 178482153, VerbindungHCID 178523075HCID 178523075, Verbindung

Produkt 1

HCID 178482154HCID 178482154, VerbindungAusbeute 25,3 %

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)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)methanamine (59 mg, 0.14 mmol), 5-Chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (63 mg, 0.18 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (100 mg, 0.72 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 (15 mg). MS 424.1 and 426.1 (M+H, Cl pattern).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1d7012d53bfe4c99b960f5cfad4258ed
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763608B2

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