Iodine → 6-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine

HRID 1892369Notes

Reaction equation

HRID 1892369 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.II.[PH2](=O)O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]([CH3:24])[N:18]=[CH:17]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 4124402Phosphinic AcidHCID 581475401-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol

Product 1

HCID 581475176-Chloro-3-(1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazineYield 85.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)ethanol (1.1 g, 3.18 mmol), diiodine (2.019 g, 7.95 mmol) and phosphinic acid (0.840 g, 12.73 mmol) in acetic acid (10 mL) was heated at 120° C. for 5 h. After cooling, the reaction mixture was concentrated in vacuo. The residue was taken with water and adjusted to pH 8 with aqueous NaOH. Then the mixture was extracted with DCM, dried over Na2SO4 and concentrated. The residue was purified with column chromatography (MeOH:EtOAc) to give 900 mg (60%) of the title compound. LCMS (method B): [MH]+=330, tR=2.59 min.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionThen the mixture was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified with column chromatography (MeOH:EtOAc)

Sources & evidence

ORD record
ord-178b13eb84844accabe36a88da60a5a2
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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