Bromine → HCID 11492197, compound

HRID 1765030Notes

Reaction equation

HRID 1765030 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.C([O-])(=O)C.[Na+].[Br:16]Br>C(O)(=O)C>[Br:16][C:8]1[N:5]2[N:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]2=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 20076587HCID 20076587, compound

Product 1

HCID 11492197HCID 11492197, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 7-methylimidazo[1,2-b]pyridazine (30.1 mg, 0.226 mmol) (prepared as described by Pollak et al, Tetrahedron, 1968, 24, 2623) and sodium acetate (27.4 mg, 0.334 mmol) in glacial acetic acid (1 ml) was added dropwise, over 2 min, bromine (12.2 μl, 0.237 mmol). The mixture was stirred at room temperature for 20 min, then partitioned carefully between saturated aqueous NaHCO3 (15 ml) and ethyl acetate (20 ml). The aqueous layer, which had a pH of 9, was extracted further with ethyl acetate (2×20 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate) to leave 47.3 mg (99%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 2.45 (3H, s), 7.70 (2H, s), 8.30 (1H, s).

Workup

  1. custompartitioned carefully between saturated aqueous NaHCO3 (15 ml) and ethyl acetate (20 ml)
  2. extractionwas extracted further with ethyl acetate (2×20 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, ethyl acetate)

Sources & evidence

ORD record
ord-860f542a034d4ad78955dd1affa6fee0
Source dataset
uspto-grants-2007_06
Patent number
US07226922B2

Reaction notes

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