Sodium Iodide → HCID 19784154, compound

HRID 257263Notes

Reaction equation

HRID 257263 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)O)[CH3:2].[I-].[Na+].Cl[Si](Cl)(C)C>C(#N)C>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6398DichlorodimethylsilaneHCID 197841501-(2-Ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)-1-(4-hydroxyphenyl)methanol

Product 1

HCID 19784154HCID 19784154, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 2.607 g (8.8 mmol) of the product of Step D and 5.257 g (35.1 mmol) of sodium iodide in 12 mL of acetonitrile was added 2.13 mL (17.5 mmol) of dichlorodimethylsilane via syringe under a nitrogen atmosphere. The reaction mixture which immediately darkened was stirred for 20 min at room temperature, then partitioned between EtOAc and brine. The organic layer was washed with aqueous sodium bicarbonate, 10% aqueous sodium thiosulfate, then dried (MgSO4), filtered and evaporated. The residue was crystallized from EtOAc-hexane to afford 2.214 g (90%) of the title compound as a pale yellow solid.

Workup

  1. custompartitioned between EtOAc and brine
  2. washThe organic layer was washed with aqueous sodium bicarbonate, 10% aqueous sodium thiosulfate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-f6b530b416b44a3bba96eeee597fca5e
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Reaction notes

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