Sodium Iodide → HCID 21464415, compound

HRID 1940922Notes

Reaction equation

HRID 1940922 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([F:10])[C:5]=1[NH:11]C(=O)OC(C)(C)C)[CH3:2].[I-].[Na+].C[Si](Cl)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:11][C:5]1[C:6]([F:10])=[N:7][CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 21464420HCID 21464420, compound

Product 1

HCID 21464415HCID 21464415, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 19 g (74 mmol) of t-butyl N-(4-ethoxy-2-fluoro-3-pyridinyl)carbamate and 12.2 g (81.5 mmol) of sodium iodide in 400 mL of dry acetonitrile was added with stirring 8.9 g (81.5 mmol) of trimethylsilyl chloride. The mixture was allowed to react for 4 hr and then a 100 mL solution of aqueous sodium bicarbonate was added with stirring. The resulting mixture was extracted with 1 L of ether and the ether extract was dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by column chromatography to obtain 6.3 g (55 percent of theory) of the title compound as a colorless solid melting at 76°-77° C.

Workup

  1. customto react for 4 hr
  2. extractionThe resulting mixture was extracted with 1 L of ether
  3. extractionthe ether extract
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7596c8650cc34f11bd1cd1b8d83dbb07
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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