Sodium Iodide → HCID 22672623, compound

HRID 1006683Notes

Reaction equation

HRID 1006683 reaction equation
[Cl:1][CH2:2][C:3]1[C:4]2[N:5]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(C)=O.C(Cl)Cl>[ClH:1].[CH3:12][C:10]1[N:11]=[C:4]2[C:3]([CH2:2][NH:17][C:16]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:15]=3[CH3:14])=[CH:8][CH:7]=[CH:6][N:5]2[C:9]=1[CH3:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 68962,6-DimethylanilineHCID 10340Sodium CarbonateHCID 22672600HCID 22672600, compound

Product 1

HCID 22672623HCID 22672623, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

8-chloromethyl-2,3-dimethylimidazo[1,2-a]pyridine (0.06 g, 0.31 mmol), 2,6-dimethylaniline (0.039 g, 0.32 mmol), sodium carbonate (0.15 g, 1.4 mmol) and sodium iodide (0.06 g, 0.4 mmol) in acetone (3 ml) was stirred for 20 h. at room temperature. Methylene chloride was added and the solids were isolated by filtration and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (2:1). The oily product was solved in methylene chloride and treated with HCl/diethyl ether to give the title compound, 0.02 g. (18%)

Workup

  1. customthe solids were isolated by filtration
  2. customthe solvents were evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. additiontreated with HCl/diethyl ether

Sources & evidence

ORD record
ord-62e0080244874d91a9aadc1e3a5fc360
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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