2-Fluoro-4-nitrophenol → 5-Chloro-4-(2-fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine

HRID 347519

Reaktionsgleichung

Reaktionsgleichung von HRID 347519
Cl[C:2]1[C:7]2=[C:8]([Cl:11])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[OH:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][N:6]2[C:7]=1[C:2]([O:22][C:14]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:13]=1[F:12])=[N:3][CH:4]=[N:5]2

Komponenten

5

Edukt 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 210816694,5-Dichloropyrrolo[2,1-f][1,2,4]triazine

Produkt 1

HCID 210816995-Chloro-4-(2-fluoro-4-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazineAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4,5-dichloropyrrolo[2,1-f][1,2,4]triazine (3.73 g, 19.8 mmol), 2-fluoro-4-nitrophenol (3.43 g, 21.8 mmol) and potassium carbonate (5.47 g, 39.6 mmol) in DMF (100 mL) was stirred at 60° C. for 1 h. After cooling to rt, the reaction was filtered through a short plug of silica gel with ethyl acetate and then concentrated in vacuo. The crude product was purified by recrystallization from ethyl acetate/hexanes (1:1) to give the title compound (4.37 g, 71%) as a white solid. 1H NMR (CDCl3) δ 8.22–8.17 (m, 2H), 7.92 (s, 1H), 7.77 (d, 1H, J=2.8 Hz), 7.58 (t, 1H, J=7.2 Hz), 6.87 (d, 1H, J=3.2 Hz); MS(ESI+) m/z 309.3 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction was filtered through a short plug of silica gel with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by recrystallization from ethyl acetate/hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-beb7dbbf2c0a427cae54be6596f241ff
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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