Sodium Iodide → HCID 135530195, compound

HRID 1921355Notes

Reaction equation

HRID 1921355 reaction equation
[CH2:1]([C:3]1[C:4]([O:16]C)=[N:5][C:6]([CH3:15])=[C:7]([C:9]2[O:10][C:11]([CH3:14])=[N:12][N:13]=2)[CH:8]=1)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:3]1[C:4](=[O:16])[NH:5][C:6]([CH3:15])=[C:7]([C:9]2[O:10][C:11]([CH3:14])=[N:12][N:13]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 67492395HCID 67492395, compound

Product 1

HCID 135530195HCID 135530195, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)pyridine (95 mg, 0.408 mmol) and sodium iodide (182 mg, 1.21 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (3 mL) followed by chlorotrimethylsilane (156 μL, 1.24 mmol). The reaction mixture is stirred at 50° C. under nitrogen for 2.5 hr. The reaction mixture is allowed to cool and then quenched with water (0.5 mL). After stirring for 30 min the mixture is evaporated. The residue is partitioned between water and dichloromethane and the mixture treated with a little sodium bisulfite to decolorize. The dichloromethane layer is separated and the aqueous layer is extracted with five portions of dichloromethane. The combined dichloromethane layer is washed with two portions of aqueous sodium hydroxide (1M), then dried over magnesium sulfate and evaporated to give an orange residue. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (30:1). The clean fractions containing the product are combined and evaporated to give 3-ethyl-6-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyridin-2-one (38 mg, 43% yield) as a white solid. LC/MS: RT: 2.10 min, MS: m/e=220 (M+H); 1H NMR (300 MHz, CDCl3, δ, ppm): 12.24 (1H, s), 7.76 (1H, s), 2.76 (3H, s), 2.61 (2H, q), 2.61 (3H, s), 1.25 (3H, t).

Workup

  1. temperatureto cool
  2. customquenched with water (0.5 mL)
  3. stirringAfter stirring for 30 min the mixture
  4. customis evaporated
  5. customThe residue is partitioned between water and dichloromethane
  6. additionthe mixture treated with a little sodium bisulfite
  7. customThe dichloromethane layer is separated
  8. extractionthe aqueous layer is extracted with five portions of dichloromethane
  9. washThe combined dichloromethane layer is washed with two portions of aqueous sodium hydroxide (1M)
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customto give an orange residue
  13. customThe crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (30:1)
  14. additionThe clean fractions containing the product
  15. customevaporated

Sources & evidence

ORD record
ord-98325f4c6fb84b6ca9aa9553c217b84b
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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