Bromine → 2-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol

HRID 347701Notes

Reaction equation

HRID 347701 reaction equation
[N:1]1[N:2]2[CH:13]=[CH:12][N:11]=[C:3]2[N:4]=[C:5]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:6]=1.C([O-])(=O)C.[Na+].[Br:19]Br>C(O)(=O)C>[Br:19][C:13]1[N:2]2[N:1]=[CH:6][C:5]([C:7]([OH:10])([CH3:9])[CH3:8])=[N:4][C:3]2=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 11218170HCID 11218170, compound

Product 1

HCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olYield 77.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 2-(imidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (5.55 g, 31.1 mmol) in acetic acid (100 ml) was added sodium acetate (3.83 g, 46.7 mmol), then, dropwise over 5 min, a solution of bromine (1.77 ml, 34.4 mmol) in acetic acid (12 ml). The solution was stirred at room temperature for 25 min, then partitioned between saturated aqueous NaHCO3 (2 l) and ethyl acetate (1 l). The aqueous layer (pH 7) was further extracted with ethyl acetate (1 l), and the combined organic extracts were dried (Na2SO4) and evaporated iii, vacuo. The residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2) to afford 6.17 g (77%) of the title compound as a yellow solid: 1H NMR (360 MHz, CDCl3) δ 1.70 (6H, s), 3.12 (1H, br s), 7.95 (1H, s), 8.80 (1H, s).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 (2 l) and ethyl acetate (1 l)
  2. extractionThe aqueous layer (pH 7) was further extracted with ethyl acetate (1 l)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customevaporated iii, vacuo
  5. customThe residue was purified by flash chromatography (silica gel, 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-17b9a03fdfd64034b6058079b299ca3f
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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