Sodium Iodide → HCID 135438447, compound

HRID 1921365Notes

Reaction equation

HRID 1921365 reaction equation
[CH2:1]([C:3]1[C:4]([O:16]C)=[N:5][C:6]([CH3:15])=[C:7]([C:9]2[O:13][N:12]=[C:11]([CH3:14])[N:10]=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:13][N:12]=[C:11]([CH3:14])[N:10]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 67492104HCID 67492104, compound

Product 1

HCID 135438447HCID 135438447, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl) pyridine (50 mg, 0.215 mmol) and sodium iodide (96 mg, 0.64 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise chlorotrimethylsilane (82 μL, 0.653 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 7 hr. The reaction mixture is allowed to cool and then quenched with water (0.5 mL). After stirring for 30 min the mixture 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 four further portions of dichloromethane. The combined organic layer is dried over magnesium sulfate and evaporated. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). Fractions containing the product are combined and the solvent evaporated to give 3-ethyl-6-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-pyridin-2-one (41 mg, 88% yield) as a white solid. LC/MS: RT: 2.44 min, MS: m/e=220 (M+H); 1H NMR (CDCl3, δ, ppm): 12.49 (1H, s), 7.92 (1H, s), 2.79 (3H, s), 2.61 (2H, q), 2.45 (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 partitioned between water and dichloromethane
  5. additionthe mixture treated with a little sodium bisulfite
  6. customThe dichloromethane layer is separated
  7. extractionthe aqueous layer is extracted with four further portions of dichloromethane
  8. dry with materialThe combined organic layer is dried over magnesium sulfate
  9. customevaporated
  10. customThe crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1)
  11. additionFractions containing the product
  12. customthe solvent evaporated

Sources & evidence

ORD record
ord-18261b3b497c46819baef3d53550eb99
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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