Sodium Azide → 4-Azidomethyl-2-bromo-6-methyl-pyridine

HRID 559711Notes

Reaction equation

HRID 559711 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[C:4]([CH3:14])[N:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:8][C:6]1[CH:5]=[C:4]([CH3:14])[N:3]=[C:2]([Br:1])[CH:7]=1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59278256Methanesulfonic acid 2-bromo-6-methyl-pyridin-4-ylmethyl ester

Product 1

HCID 592785094-Azidomethyl-2-bromo-6-methyl-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methanesulfonic acid 2-bromo-6-methyl-pyridin-4-ylmethyl ester (410 mg, 1.46 mmol) in DMF (2.0 mL) was added sodium azide (238 mg, 3.66 mmol). After 15 hours, the reaction was quenched with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was passed through a pad of silica gel eluting with 30% ethyl acetate in heptane to afford 4-azidomethyl-2-bromo-6-methyl-pyridine.

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc02b62de0fd43fb8d9680707dd6633b
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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