Diethyl Ether → HCID 21464340, compound

HRID 977052Notes

Reaction equation

HRID 977052 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].[CH2:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([F:16])[C:11]=1[NH:17]C(=O)OC(C)(C)C)[CH3:9].CCOCC>C(#N)C>[NH2:17][C:11]1[C:12]([F:16])=[N:13][CH:14]=[CH:15][C:10]=1[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 21464400HCID 21464400, compound

Product 1

HCID 21464340HCID 21464340, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl chloride (2.2 g, (0.18 mmol) and sodium iodide (2.7 g, 0.18 mmol) were added to a solution of 3.6 g (0.15 mmol) of t-butyl N-(4-ethyl-2-fluoro-3-pyridyl)carbamate in 50 mL of dry acetonitrile with stirring at ambient temperature. After 2 hours the mixture was poured into ether and the resulting solution was washed with dilute aqueous sodium bisulfite, dried over magnesium sulfate, and filtered. The liltrate was concentrated by evaporation under reduced pressure to obtain an oil. This oil was purified by column chromatography to obtain 1.6 g (76 percent of theory) of the title compound as a gold oil.

Workup

  1. washthe resulting solution was washed with dilute aqueous sodium bisulfite
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe liltrate was concentrated by evaporation under reduced pressure
  5. customto obtain an oil
  6. customThis oil was purified by column chromatography

Sources & evidence

ORD record
ord-126e53e929b8402aa3c26dc83a21c580
Source dataset
uspto-grants-1997_03
Patent number
US05614469

Reaction notes

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