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

HRID 347695Notes

Reaction equation

HRID 347695 reaction equation
[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

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 11622469HCID 11622469, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-448ce92794a645d58d30fda285d12c83
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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