Sodium hydride → 6-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine

HRID 1072914Notes

Reaction equation

HRID 1072914 reaction equation
[C:1]([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Br:14])[N:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C)C=O>[Br:14][C:7]1[N:6]=[C:5]([N:4]([CH2:20][C:19]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:18]=2[Cl:17])[C:1](=[O:3])[CH3:2])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 130420934-(Bromomethyl)-3-chlorobenzonitrileHCID 223878242-Acetamido-6-bromo-3-nitropyridine

Product 1

HCID 223878586-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(Acetamido)-6-bromo-3-nitropyridine (3.21 g) was dissolved in dry N,N-dimethylformamide (16 ml), and sodium hydride (60% in oil, 326 mg) was added under ice-cooling. The mixture was stirred for 30 min. A solution of 2-chloro-4-cyanobenzyl bromide (2.34 g) in dry N,N-dimethylformamide (4 ml) was dropwise added at the same temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the objective compound (4.17 g) as a pale-yellow powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-5350cfc775f74876bebab29beca2eb42
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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