8-Hydroxyquinoline → HCID 24760453, Verbindung

HRID 499773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499773
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)=[O:8])=[CH:4][CH:3]=1.I[C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]2=[O:29])=[CH:19][C:18]=1[F:30].OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]4=[O:29])=[CH:19][C:18]=3[F:30])[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 593866611-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzeneHCID 178523075HCID 178523075, Verbindung

Produkt 1

HCID 24760453HCID 24760453, 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 5-chloro-N-((1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 3-1 prepared above (0.940 g, 2.64 mmol), 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene 3-2 prepared above (0.820 g, 2.60 mmol), 8-hydroxyquinoline (0.066 g, 0.45 mmol) and K2CO3 (0.630 g, 4.56 mmol) in DMSO (8 mL) was degassed with Ar before being charged with CuI (0.090 g, 0.47 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (0.480 g). MS 429.0 and 431.0 (M+H, Cl pattern).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-74bd7de583274c0cacb8b2b8679859d3
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767697B2

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