Sodium Azide → 3-(Azidomethyl)-5-bromopyridine

HRID 1819407Notes

Reaction equation

HRID 1819407 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]OS(C)(=O)=O)[CH:5]=[N:6][CH:7]=1.[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C.O>[N:14]([CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57885697HCID 57885697, compound

Product 1

HCID 576405383-(Azidomethyl)-5-bromopyridineYield 60.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of crude methanesulfonic acid 5-bromo-pyridin-3-ylmethyl ester (4.20 g) in DMF (60 mL) was added NaN3 (10.0 g, 153.8 mmol). The mixture was stirred under N2 overnight then diluted with water. The mixture was extracted with EtOAc (2×300 mL) and the combined organic layers washed with water before drying over Na2SO4. The solution was concentrated in vacuo to afford crude 3-azidomethyl-5-bromo-pyridine (2.04 g) as a dark brown oil. This crude material was used directly in the next step.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×300 mL)
  2. washthe combined organic layers washed with water
  3. dry with materialbefore drying over Na2SO4
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-e29ad2da9f9941f18591876a464be5b9
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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