Bromine → 7-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazine

HRID 347695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347695
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[N:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[N:4]=1.C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:9]1[N:6]2[N:7]=[CH:8][C:3]([C:2]([F:1])([F:12])[F:13])=[N:4][C:5]2=[N:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 116224693-Trifluoromethyl-imidazo[1,2-B][1,2,4]triazine

Produkt 1

HCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.2211 g, 1.18 mmol) in acetic acid (6 ml) was added sodium acetate (0.1470 g, 1.79 mmol), then bromine (90.8 μl, 1.76 mmol). The solution was stirred at room temperature for 6 h, then partitioned between saturated aqueous NaHCO3 (100 ml) and ethyl acetate (100 ml). The aqueous layer (pH 9) was further extracted with ethyl acetate (100 ml), and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane) to afford 0.2073 g (66%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 8.30 (1H, s), 8.83 (1H, s).

Aufarbeitung

  1. custompartitioned between saturated aqueous NaHCO3 (100 ml) and ethyl acetate (100 ml)
  2. extractionThe aqueous layer (pH 9) was further extracted with ethyl acetate (100 ml)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 25% EtOAc/isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-448ce92794a645d58d30fda285d12c83
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176203B2

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