Reaction #465968

Reaction equation

methyl 4,6-dibromo-3-chloropyridine-2-carboxylate

sodium azide

→

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

Yield 66.7%

Solvents

water

DMF

Conditions

Workup

1. 1
   Temperaturecooled to 0° C. for 1 hr
2. 2
   OtherThe solid was collected

Procedure

To a solution of methyl 4,6-dibromo-3-chloropyridine-2-carboxylate (6.0 g 0.018 mol) in DMF (50 mL) was added sodium azide (2.0 g 0.03 mol) and the solution warmed to 50° C. for 1 hr. The reaction was diluted with water (200 mL) and cooled to 0° C. for 1 hr. The solid was collected to give methyl 4-azido-6-bromo-3-chloropyridine-2-carboxylate (4.4 g, 0.012 mol, 66%); mp 84-86° C.

Source