Water → 3-Bromo-6-fluoroimidazo[1,2-b]pyridazine

HRID 870619Notes

Reaction equation

HRID 870619 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[Br:11]Br.O>C(O)(=O)C>[Br:11][C:8]1[N:6]2[N:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 151444366-Fluoroimidazo[1,2-b]pyridazine

Product 1

HCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazineYield 27.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an ambient temperature, stirred solution of 6-fluoro-imidazo[1,2-b]pyridazine (2.1 g, 15.3 mmol) in glacial acetic acid (20 mL) was slowly added bromine (2.5 g, 15.3 mmol). Upon completion of this addition the reaction solution was poured into water and extracted with ethyl acetate. The extract was dried (MgSO4) and flash chromatographed (silica gel, eluted with 30% (v/v) ethyl acetate/hexanes) to provide 0.9 g of 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine. LRMS (ESI) m/z 215.9/217.9 [(M+H)]+, calc'd for C6H3BrFN3: 216.01.

Workup

  1. additionUpon completion of this addition the reaction solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4) and flash
  4. customchromatographed
  5. wash(silica gel, eluted with 30% (v/v) ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ceb6964eec0342d6a82be2c5fe62292a
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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