Bromine → HCID 11459593, Verbindung

HRID 891854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891854
[F:1][C:2]([C:5]1[CH:10]=[N:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[N:6]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:11]1[N:8]2[N:9]=[CH:10][C:5]([C:2]([F:1])([CH3:4])[CH3:3])=[N:6][C:7]2=[N:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 222400983-(1-Fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine

Produkt 1

HCID 11459593HCID 11459593, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine (0.6208 g, 3.45 mmol) in acetic acid (15 ml) was added sodium acetate (0.4251 g, 5.18 mmol), then, dropwise over 5 min, a solution of bromine (0.195 ml, 3.78 mmol) in acetic acid (2 ml). The solution was stirred at room temperature for 30 min, then partitioned between saturated aqueous NaHCO3 (300 ml) and ethyl acetate (150 ml). The aqueous layer (pH 7) was further extracted with ethyl acetate (2×150 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 0.8437 g (95%) of the title compound as a yellow solid: 1H NMR (360 MHz, CDCl3) δ 1.82 (6H, d, J 22.1), 7.99 (1H, s), 8.81 (1H, d, J 1.1).

Aufarbeitung

  1. custompartitioned between saturated aqueous NaHCO3 (300 ml) and ethyl acetate (150 ml)
  2. extractionThe aqueous layer (pH 7) was further extracted with ethyl acetate (2×150 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-cb3a05a7ed7447f9a7db4388bc4ce624
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005431B2

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