Reaction #465971

Reaction equation

sodium azide

Methyl 4,6-dibromo-3-methoxypyridine-2-carboxylate

H2O

→

orange oil

Yield 57.7%

Methyl 4-Azido-6-bromo-3-methoxypyridine-2-carboxylate

Yield 57.7%

Solvents

DMF

Conditions

Workup

1. 1
   Otherto form a homogeneous solution
2. 2
   OtherReaction mixture
3. 3
   workup.ADDITIONadded to a flask
4. 4
   Extractionextracted with ethyl acetate (3×50 mL)
5. 5
   Washback washed with H2O
6. 6
   Dryingdried (MgSO4)
7. 7
   Concentrationconcentrated

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).

Source