Water → Methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylate

HRID 378789Notes

Reaction equation

HRID 378789 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14].[N-:15]=[N+:16]=[N-:17].[Na+].O>CN(C=O)C>[N:15]([C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21696615Methyl 4,6-dibromo-3-methoxypyridine-2-carboxylate

Product 1

HCID 21696596Methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylateYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4,6-dibromo-3-methoxypyridine-2-carboxylate (0.980 g, 3.02 mmol) was dissolved in a minimum amount of DMF. Slowly sodium azide (0.216 g, 3.32 mmol) was added followed by H2O to form a homogeneous solution. The reaction mixture was heated to 60° C. and stirred for 2 days. Reaction mixture added to a flask filled with ice water and extracted with ethyl acetate (3×50 mL). Extracts were combined and back washed with H2O, dried (MgSO4) and concentrated to give 0.500 g of an orange oil. 1H NMR(CDCl3): δ 3.90 (s, 3H); 3.95 (s, 3H); 7.20 (s, 1H).

Workup

  1. customto form a homogeneous solution
  2. customReaction mixture
  3. additionadded to a flask
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washback washed with H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-63cd3b626c584dd9855e043b59d2149d
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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