Iodine → (Rac)-6-chloro-3-[1-(3-methyl-3h-benzoimidazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine

HRID 69230Notes

Reaction equation

HRID 69230 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:23]=[CH:22][C:17]4[N:18]=[CH:19][N:20]([CH3:21])[C:16]=4[CH:15]=3)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.II.O[PH2]=O.[OH-].[Na+].C([O-])(O)=O.[Na+]>CC(O)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:14]3[CH:23]=[CH:22][C:17]4[N:18]=[CH:19][N:20]([CH3:21])[C:16]=4[CH:15]=3)[CH3:12])=[CH:9][N:10]=2)[N:7]=1

Participants

8

Reactant 5

HCID 807IodineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 4124402Phosphinic AcidHCID 87523187(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(3-methyl-3h-benzoimidazol-5-yl)-ethanol

Product 1

HCID 87524205(Rac)-6-chloro-3-[1-(3-methyl-3h-benzoimidazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a microwave vial, (rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(3-methyl-3H-benzoimidazol-5-yl)-ethanol (Stage 185.3, 650 mg, 1.507 mmol) was dissolved in AcOH (15 mL) under Argon. Iodine (1.148 g, 4.52 mmol) and H3PO2 (1.233 mL of a 50% aqueous solution, 11.3 mmol) were added and the mixture was submitted to MW-irradiation at 150° C. for 10 min. The mixture was diluted with water. It was basified until pH 5 with NaOH 10 M and then saturated NaHCO3 sol. until pH 7-8. It was then extracted with EtOAc one time. The organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. It was then dried under vacuum overnight to afford the title compound as a foam (tR 2.12 min (conditions 8), MH+=312).

Workup

  1. extractionIt was then extracted with EtOAc one time
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customIt was then dried under vacuum overnight

Sources & evidence

ORD record
ord-07e1d19cae974f2cbf4f07c9c5193403
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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