Sodium Iodide → HCID 135509914, compound

HRID 1921372Notes

Reaction equation

HRID 1921372 reaction equation
[CH2:1]([C:3]1[C:4]([O:16]C)=[N:5][C:6]([CH3:15])=[C:7]([C:9]2[N:13]=[C:12]([CH3:14])[O:11][N:10]=2)[CH:8]=1)[CH3:2].[I-].[Na+].C(#N)C.Cl[Si](C)(C)C>O.CCOCC>[CH2:1]([C:3]1[C:4](=[O:16])[NH:5][C:6]([CH3:15])=[C:7]([C:9]2[N:13]=[C:12]([CH3:14])[O:11][N:10]=2)[CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 67492482HCID 67492482, compound

Product 1

HCID 135509914HCID 135509914, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-pyridine (47 mg, 0.202 mmol) and sodium iodide (91 mg, 0.607 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise addition of chlorotrimethylsilane (76 μL, 0.605 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 15 hr. The reaction mixture is allowed to cool, diluted with water and the resulting mixture is extracted with four portions of dichloromethane. The combined extracts are dried over magnesium sulfate and evaporated to leave an orange residue. The crude product is purified by flash chromatography on a 2-gram silica gel cartridge by elution with heptane:dichloromethane: (1:1). Fractions containing the product are combined, the solvent evaporated and the residue triturated with ether to 3-ethyl-6-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-1H-pyridin-2-one (25 mg, 58% yield) as a light yellow powder. LC/MS: RT: 2.39 min, MS: m/e=220 (M+H); 1H NMR (CDCl3, δ, ppm): 12.14 (1H, s), 7.89 (1H, s), 2.70 (3H, s), 2.64 (3H, s), 2.61 (2H, q), 1.24 (3H, t).

Workup

  1. temperatureto cool
  2. extractionthe resulting mixture is extracted with four portions of dichloromethane
  3. dry with materialThe combined extracts are dried over magnesium sulfate
  4. customevaporated
  5. customto leave an orange residue
  6. customThe crude product is purified by flash chromatography on a 2-gram silica gel cartridge by elution with heptane
  7. additionFractions containing the product
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-acf9239ad183429983356a90ef81d99a
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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