8-Hydroxyquinoline → 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazole

HRID 573860

Reaktionsgleichung

Reaktionsgleichung von HRID 573860
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[CH:23][NH:22][N:21]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].OC1C=CC=C2C=1N=CC=C2>CN(C)C=O.O.[Cu]I>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:2]3[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=3)[N:21]=2)=[CH:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 469487345-(4-Bromophenyl)-1H-1,2,4-triazole

Produkt 1

HCID 904040773-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazoleAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 1-iodo-4-(trifluoromethoxy)benzene (15.0 g, 52.0 mmol) in dimethylformamide (90 mL) and water (10 mL) was added 3-(4-bromophenyl)-1H-1,2,4-triazole (C51) (11.0 g, 49.0 mmol), cesium carbonate (34.0 g, 104 mmol), copper(I) iodide (2.80 g, 14.7 mmol), and 8-hydroxyquinoline (2.20 g, 15.0 mmol), and the solution was heated at 140° C. for 8 hours. The cooled solution was decanted from a layer of solid, diluted with a ammonium hydroxide (1 N, 100 mL) solution, and extracted with of diethyl ether (2×100 mL). The combined organic layer was dried and concentrated, and the brown solid was eluted through a short silica gel column using 20% ethyl acetate/hexanes as eluent to give the title compound as a light tan solid (9.50 g, 50%): mp 111-113° C.; 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.07 (d, J=8.6 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.39 (d, J=8.8 Hz, 2H); ESIMS m/z 384 ([M+H]+).

Aufarbeitung

  1. customThe cooled solution was decanted from a layer of solid
  2. additiondiluted with a ammonium hydroxide (1 N, 100 mL) solution
  3. extractionextracted with of diethyl ether (2×100 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated
  6. washthe brown solid was eluted through a short silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-bc220f5a0064485fad3aa8cac73bb45c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029560B2

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