2-Fluoroethyl bromide → HCID 178453063, compound

HRID 1861903Notes

Reaction equation

HRID 1861903 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:18])=[S:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][CH2:22][F:23]>C(#N)C>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[NH:18])[S:17][CH2:21][CH2:22][F:23])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 129822-Fluoroethyl bromideHCID 18331431HCID 18331431, compound

Product 1

HCID 178453063HCID 178453063, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of the compound (500 mg) obtained in Example 24 and acetonitrile (20 ml) was added 1-bromo-2-fluoroethane (0.26 ml) and the reaction mixture was heated under reflux for 2 h. The reaction mixture was distilled under reduced pressure and the resulting residue was dissolved in ethyl acetate and washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution and the organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4) to give 50 mg of the titled compound (yield, 9%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. distillationThe reaction mixture was distilled under reduced pressure
  4. dissolutionthe resulting residue was dissolved in ethyl acetate
  5. washwashed successively with a saturated aqueous sodium bicarbonate solution
  6. dry with materiala saturated aqueous sodium chloride solution and the organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-bab68a44e6514ee29591856aa7ad08b0
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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