Sodium Iodide → HCID 135513085, compound

HRID 1921374Notes

Reaction equation

HRID 1921374 reaction equation
[CH2:1]([C:3]1[C:4]([O:15]C)=[N:5][C:6]([CH3:14])=[C:7]([C:9]2[N:13]=[CH:12][O:11][N:10]=2)[CH:8]=1)[CH3:2].[I-].[Na+].C(#N)C.Cl[Si](C)(C)C>O>[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[N:13]=[CH:12][O:11][N:10]=2)[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 67492215HCID 67492215, compound

Product 1

HCID 135513085HCID 135513085, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(1,2,4-oxadiazol-3-yl)pyridine (56 mg, 0.256 mmol) and sodium iodide (117 mg, 0.78 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise addition of chlorotrimethylsilane (97.5 μL, 0.776 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 16 hr. The reaction mixture is allowed to cool, diluted with water and the resulting mixture is extracted with five portions of dichloromethane. The combined extract is dried over magnesium sulfate and evaporated to leave a brown residue. This material 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-(1,2,4-oxadiazol-3-yl)-1H-pyridin-2-one (38 mg, 73% yield) as a off-white solid. LC/MS: RT: 2.27 min, m/e=206 (M+H); 1H NMR (400 MHz, δ, ppm): 12.02 (1H, s), 9.64 (1H, s), 7.74 (1H, s), 2.52 (3H, s), 2.41 (2H, q), 1.10 (3H, t).

Workup

  1. temperatureto cool
  2. extractionthe resulting mixture is extracted with five portions of dichloromethane
  3. extractionThe combined extract
  4. dry with materialis dried over magnesium sulfate
  5. customevaporated
  6. customto leave a brown residue
  7. customThis material is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1)
  8. additionFractions containing the product
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-6890a7e68e924106b72676574b062f8d
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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