Iodoethane → HCID 66997992, compound

HRID 561020Notes

Reaction equation

HRID 561020 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:20])[NH:9][CH:10]([C:12]1[CH:13]=[N:14][C:15]([F:19])=[CH:16][C:17]=1[I:18])[CH3:11])([CH3:6])([CH3:5])[CH3:4].I[CH2:22][CH3:23]>CN(C)C=O>[C:3]([O:7][C:8](=[O:20])[N:9]([CH2:22][CH3:23])[CH:10]([C:12]1[CH:13]=[N:14][C:15]([F:19])=[CH:16][C:17]=1[I:18])[CH3:11])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66738218HCID 66738218, compound

Product 1

HCID 66997992HCID 66997992, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (84.0 mg, 2.1 mmol, 60% dispersion in mineral oil) to a solution of [1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (0.37 g, 1.0 mmol) in dimethylformamide (10 mL). Stir at room temperature for 30 min. Add iodoethane (0.2 mL, 2.1 mmol). Stir for 1 hour. Quench the reaction with water. Extract with CH2Cl2. Wash the organic layer with water and saturated aqueous sodium chloride. Dry over MgSO4. After filtration, afford crude product ethyl-[1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (0.4 g, 97%) with 90% HPLC purity, MS (ES) m/z 395 [M+1]+.

Workup

  1. stirringStir for 1 hour
  2. customQuench
  3. customthe reaction with water
  4. extractionExtract with CH2Cl2
  5. washWash the organic layer with water and saturated aqueous sodium chloride
  6. dry with materialDry over MgSO4
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-67baa8792da747eda85c8fc0a371ec05
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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