Diethyl Ether → HCID 21464340, compound

HRID 2211005Notes

Reaction equation

HRID 2211005 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)OCCCC)[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 53731278HCID 53731278, 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 [-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 and the resulting solution was washed with dilute aqueous sodium bisulfite, dried over magnesium sulfate, and filtered. The filtrate 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 filtrate 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-75060c4bda3749948d415d31c3d6f40b
Source dataset
uspto-grants-1995_10
Patent number
US05461161

Reaction notes

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