Réaction #1594560

Équation de réaction

2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline

Intermediate 11

2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline

4-carboxy-2-chlorophenylboronic acid

K2CO3

HCl

→

product

Rendement 68.6%

3-chloro-4-(6-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)benzoic acid

Rendement 68.6%

Solvants

water

diethylene glycol monomethyl ether

water

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting mixture was cooled to room temperature
2. 2
   Extractionextracted with EtOAc (50 mL×3)
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe residue was purified by column chromatography on silica gel (PE/EtOAc=1/1)

Mode opératoire

A mixture of 2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline (Intermediate 11, 150 mg, 0.571 mmol), 4-carboxy-2-chlorophenylboronic acid (115 mg, 0.571 mmol), K2CO3 (160 mg, 1.14 mmol) and Pd(dppf)Cl2 (50 mg, 0.0612 mmol) in diethylene glycol monomethyl ether (2 mL) and water (0.6 mL) was stirred at 120° C. under N2 atmosphere for 2 hours. The resulting mixture was cooled to room temperature and diluted with water (50 mL), acidified with aqueous HCl (2M) until pH=5, extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=1/1) to give the product (150 mg, yield 68%) as a solid.

Source