Bromine → HCID 22329553, compound

HRID 586236Notes

Reaction equation

HRID 586236 reaction equation
[N:1]1[N:2]2[CH:9]=[CH:8][N:7]=[C:3]2[N:4]=[CH:5][CH:6]=1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C>[Br:15][C:9]1[N:2]2[N:1]=[CH:6][CH:5]=[N:4][C:3]2=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 12262392Imidazo[1,2-b][1,2,4]triazine

Product 1

HCID 22329553HCID 22329553, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of imidazo[1,2-b][1,2,4]triazine (0.206 g, 1.715 mmol), in acetic acid (5 ml) was added sodium acetate (0.211 g, 2.27 mmol), then, dropwise over 3 min, bromine (114.8 μl, 2.23 mmol). The solution was stirred at room temperature for 30 min, then partitioned between saturated aqueous NaHCO3 (200 ml) and ethyl acetate (200 ml). The organic extracts were dried (Na2SO4), silica gel added and evaporated in vacuo. The residue was purified by chromatography (silica gel, 50% EtOAc/isohexane) to afford 0.3147 g (74%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 7.25 (1H, s), 8.05 (1H, s), 8.48-8.50 (1H, m); MS (ES+) m/z 199.

Workup

  1. custompartitioned between saturated aqueous NaHCO3 (200 ml) and ethyl acetate (200 ml)
  2. dry with materialThe organic extracts were dried (Na2SO4), silica gel
  3. additionadded
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography (silica gel, 50% EtOAc/isohexane)

Sources & evidence

ORD record
ord-b011c51efb004cd48092ebf38d79657e
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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