Reaction #465974

Reaction equation

sodium bicarbonate

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

sulfuryl chloride

→

white solid

Methyl 4-Amino-6-bromo-5-chloro-3-methoxypyridine-2-carboxylate

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureThe solution was heated
2. 2
   Temperatureto reflux for 5 min
3. 3
   Extractionwas extracted with diethyl ether (3×)
4. 4
   DryingThe combined organic extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherto give a yellow solid
8. 8
   WashSolid was washed in 10% diethyl ether/petroleum ether
9. 9
   Filtrationsolid filtered

Procedure

To methyl 4-amino-6-bromo-3-methoxypyridine-2-carboxylate (1.45 g, 5.56 mmol) in 10 mL of acetonitrile was added sulfuryl chloride, in excess, via pipette until the solution remained yellow. The solution was heated to reflux for 5 min. The reaction mixture was added to saturated sodium bicarbonate and aqueous phase was extracted with diethyl ether (3×). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. Solid was washed in 10% diethyl ether/petroleum ether and solid filtered to give 0.580 g of a white solid.

Source