Sodium Iodide → HCID 57899325, compound

HRID 425756Notes

Reaction equation

HRID 425756 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:17])[C:11]2[CH2:15][O:14][C:13](=[O:16])[CH:12]=2)[CH:5]=[N:6][C:7]=1Cl.C(#N)CC.Cl[Si](C)(C)C.[I-:27].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:17])[C:11]2[CH2:15][O:14][C:13](=[O:16])[CH:12]=2)[CH:5]=[N:6][C:7]=1[I:27]

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 7854PropionitrileHCID 16752771HCID 16752771, compound

Product 1

HCID 57899325HCID 57899325, compoundYield 29.9%

Procedure

150 mg (0.55 mmol) of 4-[[(5,6-dichloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one (10), 1.2 ml of propionitrile, 140 μl of chlorotrimethylsilane (1.10 mmol) and 247 mg of sodium iodide (1.65 mmol) are heated under reflux for 2 hours. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (5:1) gives 60 mg (29% of theory) of 4-[[(5-chloro-6-iodopyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationConcentration
  3. customunder reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-d5188bbbf81049a2b178f1f462ff7f4d
Source dataset
uspto-grants-2012_01
Patent number
US08106212B2

Reaction notes

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