Sodium Iodide → (4-Iodopyridin-2-yl)methyl acetate

HRID 2218947Notes

Reaction equation

HRID 2218947 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14](Cl)[CH:13]=[CH:12][N:11]=1)(C(C)(C)C)(C)C.[I-:17].[Na+].[C:19](Cl)(=[O:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[I:17][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:9])[CH:15]=1.[I:17][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:9][O:8][C:19](=[O:21])[CH3:20])[CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 597709462-(((Tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine

Product 2

HCID 126913224-Iodo-2-methylpyridineYield 22%HCID 53427278(4-Iodopyridin-2-yl)methyl acetateYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(((Tert-butyldimethylsilyl)oxy)methyl)-4-chloropyridine (600 mg, 2.33 mmol), dry sodium iodide (5 g) and freshly distilled acetyl chloride (0.7 mL, 9.78 mmol) in 6 mL of anhydrous acetonitrile were refluxed under nitrogen for 33 hours. Aqueous 10% K2CO3/5% NaHSO3 was added and the mixture extracted three times with chloroform. After drying (Na2SO4) and evaporation of the chloroform, flash chromatography (hexane/EtOAc 9:1) yielded 110 mg (22%) of 4-Iodo-2-methylpyridine as a white solid and 290 mg (45%) of (4-iodo-2-pyridyl)methylacetate as a white solid.

Workup

  1. extractionthe mixture extracted three times with chloroform
  2. customAfter drying
  3. custom(Na2SO4) and evaporation of the chloroform, flash chromatography (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-ba3602af57394481a6bb343b80b6ab40
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

Loading…