8-Hydroxyquinoline → HCID 178474185, Verbindung

HRID 559566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559566
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](=[O:17])[CH3:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[S:23][C:22]([C:24]([NH:26][CH2:27][C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)=[O:25])=[CH:21][CH:20]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[C:15](/[N:14]=[C:9]1/[N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH:32]=[C:28]([CH2:27][NH:26][C:24]([C:22]4[S:23][C:19]([Cl:18])=[CH:20][CH:21]=4)=[O:25])[N:29]=[CH:30]3)=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=[CH:10]/1)(=[O:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 178474184HCID 178474184, VerbindungHCID 178523075HCID 178523075, Verbindung

Produkt 1

HCID 178474185HCID 178474185, VerbindungAusbeute 6,6 %

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)acetamide (120 mg, 0.27 mmol), 5-Chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 (109 mg, 0.30 mmol), 8-hydroxyquinoline (15 mg, 0.10 mmol) and K2CO3 (100 mg, 0.72 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (24 mg, 0.12 mmol). The mixture in a sealed tube was heated at 130° C. for 5 h. It was then purified by HPLC to give the titled compound (8 mg). MS 452.0 and 454.0 (M+H, Cl pattern).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bdf89772379341ea98d7d66150557a7f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063077B2

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