Bromoacetonitrile → HCID 117689869, compound

HRID 928659Notes

Reaction equation

HRID 928659 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]([F:15])[C:9]=1[F:16])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:21][C:22]#[N:23]>CN(C=O)C>[C:1]([O:5][C:6](=[O:17])[N:7]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]([F:15])[C:9]=1[F:16])[CH2:21][C:22]#[N:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 46739517tert-Butyl (5-bromo-2,3-difluorophenyl)carbamate

Product 1

HCID 117689869HCID 117689869, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution (3 mL) of tert-butyl(5-bromo-2,3-difluorophenyl)carbamate (182 mg, 0.591 mmol) in DMF was added to a suspension of 60% sodium hydride-oil dispersion (31.2 mg) in DMF, and stirred at room temperature for 15 minutes. To the reaction solution, bromoacetonitrile (0.041 mL, 0.591 mmol) was added, and stirred at room temperature for 4 hours. After quenched with a saturated aqueous ammonium chloride solution under ice-cooling, extraction was performed with ethyl acetate. The resulting organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. customAfter quenched with a saturated aqueous ammonium chloride solution under ice-
  3. temperaturecooling
  4. extractionextraction
  5. dry with materialThe resulting organic phase was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-25ccd741ac904552b662042009dd160e
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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