Sodium Iodide → HCID 22678585, compound

HRID 1837774Notes

Reaction equation

HRID 1837774 reaction equation
C(#N)C.[C:4]([C:6]1[CH:7]=[C:8]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[CH2:17][CH2:16]2)[C:9]([O:12]C)=[N:10][CH:11]=1)#[N:5].[I-].[Na+].Cl[Si](C)(C)C>O>[C:4]([C:6]1[CH:7]=[C:8]([CH2:14][N:15]2[CH2:16][CH2:17][CH:18](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[CH2:19][CH2:20]2)[C:9](=[O:12])[NH:10][CH:11]=1)#[N:5]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 6342AcetonitrileHCID 6397Chlorotrimethylsilane2×HCID 22678291HCID 22678291, compound

Product 1

HCID 22678585HCID 22678585, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetonitrile (10 ml) were added 214 mg of 1-[(5-cyano-2-methoxy-3-pyridinyl)methyl]-4-[(E)-2-(2-fluorophenyl)-1-ethenyl]piperidine, 137 mg of sodium iodide and 0.1 ml of chlorotrimethylsilane, followed by stirring at room temperature. After 5 hours, 685 mg of sodium iodide and 0.5 ml of chlorotrimethylsilane were added thereto, followed by stirring at room temperature for 20 minutes. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium carbonate, an aqueous sodium thiosulfate and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was suspended in an aqueous sodium carbonate, followed by stirring at room temperature. The crystals were collected by filtration, to give 185 mg of the title compound as a slight yellow powder.

Workup

  1. stirringby stirring at room temperature for 20 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous sodium carbonate
  4. dry with materialan aqueous sodium thiosulfate and brine, and then dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. stirringby stirring at room temperature
  7. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-987e50052e56493bb64a19d70e4c006d
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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