Sodium Iodide → HCID 22672638, compound

HRID 1006684Notes

Reaction equation

HRID 1006684 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[OH:11].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:31][C:32]1[C:33]2[N:34]([C:38]([CH3:42])=[C:39]([CH3:41])[N:40]=2)[CH:35]=[CH:36][CH:37]=1.[I-].[Na+]>COCCOC.CO.CN(C)C=O>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[O:11][CH2:31][C:32]1[C:33]2[N:34]([C:38]([CH3:42])=[C:39]([CH3:41])[N:40]=2)[CH:35]=[CH:36][CH:37]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 113352,6-DimethylphenolHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 22672600HCID 22672600, compound

Product 1

HCID 22672638HCID 22672638, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of potassium hydroxide (0.035 g, 0.62 mmol), 2,6-dimethylphenol (0.075 g, 0.62 mmol) and 18-crown-6 (0.035 g) in 1,2-dimethoxyethane was added 8-chloromethyl-2,3-dimethylimidazo[1,2-a]pyridine (0.1 g, 0.51 mmol) in 1,2-dimethyxyethane (3 ml). The reaction mixture was stirred for 1.5 h. at room temperature and sodium iodide (0.035 g, 0.23 mmol) was added. The mixture was stirred for 3.5 h. and N,N-dimethylformamide (1 ml) and methanol were added and the solids were isolated by filtration. The filtrate was evaporated under reduced pressure, the residue was solved in methylene chloride and washed with saturated sodium bicarbonate. The organic layer was separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:3.5) as eluent to give 0.11 (78%) of the title compound.

Workup

  1. stirringThe mixture was stirred for 3.5 h.
  2. customthe solids were isolated by filtration
  3. customThe filtrate was evaporated under reduced pressure
  4. washwashed with saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce07ac2b004d424998a88cc310d23292
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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