Reaction #465972

Reaction equation

Ethyl acetate

water

methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylate

NaBH4

→

white solid

Yield 66.0%

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

Yield 66.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherthe phases were separated
2. 2
   WashThe organic phase was washed with H2O
3. 3
   Dryingdried (MgSO4)
4. 4
   Concentrationconcentrated to dryness in vacuo
5. 5
   OtherThe residue was purified by chromatography (silica gel)
6. 6
   WashElution with 100% ethyl acetate

Procedure

To methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylate (0.500 g, 1.74 mmol) in 10 mL of methanol was added NaBH4 (0.046 g, 1.22 mmol). The reaction mixture was stirred at room temperature for 10 min. Ethyl acetate and water were added and the phases were separated. The organic phase was washed with H2O, dried (MgSO4) and concentrated to dryness in vacuo. The residue was purified by chromatography (silica gel). Elution with 100% ethyl acetate gave 0.300 g of a white solid. 1H NMR(CDCl3): δ 3.90 (s, 1H); 3.95 (s, 1H); 4.60 (s, 2H); 6.85 (s, 1H).

Source