Sodium Hydroxide → 3-Bromoimidazo(1,2-b)pyridazine

HRID 2046401

Reaction equation

HRID 2046401 reaction equation
[Br:1]Br.[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[N:7]2.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:5]1[N:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:11]2=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24408BromineHCID 136599Imidazo(1,2-b)pyridazineHCID 516892Sodium Bicarbonate

Product 1

HCID 128723193-Bromoimidazo(1,2-b)pyridazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bromine (0.649 mL, 12.6 mmol) was added dropwise to a stirred mixture of Imidazo[1,2-b]pyridazine (1.0 g, 8.39 mmol) in acetic acid (42 ml) and the mixture was stirred at room temperature for 1 h. The mixture was neutralized with 1 N sodium hydroxide (100 mL) and solid sodium hydroxide, poured into ethyl acetate and sodium bicarbonate solution, and extracted with ethyl acetate (3×200 mL). The combined organics were washed with brine, dried (MgSO4), and concentrated to afford the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 8.66 (d, 1H); 8.17 (d, 1H); 7.93 (s, 1H); 7.31 (dd, 1H). LRMS (APCI) calc'd for (C6H5BrN3) [M+H]+, 198.0. found 198.0.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-891d5284fa094b1f980f86328bdd5ba6
Source dataset
uspto-grants-2013_11
Patent number
US08592425B2

Linked notes

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