Sodium Azide → 2-(Azidomethyl)-6-bromopyridine

HRID 386039Notes

Reaction equation

HRID 386039 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12]Br)[N:7]=1>CS(C)=O.O>[N:1]([CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([Br:5])[N:7]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 453574032-(Azidomethyl)-6-bromopyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium azide (3.11 g, 47.8 mmol) and 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (4.00 g, 15.94 mmol) were combined in DMSO (30 mL) and stirred at room temperature for 4 h. The mixture was subsequently diluted with water and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography (0-10% EtOAc/hexanes) to yield the title compound as a colorless oil.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d448377e4ff64587934e65ffcfee5011
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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