Réaction #70280

Équation de réaction

Water

6-chloropyridin-3-amine

2-bromo-5-methylbenzoic acid

K2CO3

→

2-(6-Chloropyridin-3-ylamino)-5-methylbenzoic acid

Rendement 46.0%

Solvants

1,2-dimethoxyethane

Conditions de réaction

Traitement

1. 1
   Filtrationthe mixture was filtered through celite
2. 2
   workup.ADDITIONHCl 2N aqueous solution was added until pH 6
3. 3
   Autrethe solid formed
4. 4
   Filtrationwas filtered off
5. 5
   AutreThe crude was purified by chromatography
6. 6
   Lavageeluting with DCM/MeOH
7. 7
   Autremixtures affording 1.40 g (yield 46%)

Mode opératoire

A mixture of 6-chloropyridin-3-amine (11.67 mmol, 1.5 g) and 2-bromo-5-methylbenzoic acid (23.34 mmol, 5.02 g), Cu (1.17 mmol, 0.1 g), Cu2O (0.58 mmol, 0.1 g) and K2CO3 (23.34 mmol, 3.2 g) in 1,2-dimethoxyethane (15 ml) was heated at 130° C. for 16 hours, under argon atmosphere. Water was added and the mixture was filtered through celite. HCl 2N aqueous solution was added until pH 6 and the solid formed was filtered off. The crude was purified by chromatography eluting with DCM/MeOH mixtures affording 1.40 g (yield 46%).

Source