Реакция #1594560

Уравнение реакции

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

Intermediate 11

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

4-carboxy-2-chlorophenylboronic acid

K2CO3

HCl

→

product

Выход 68.6%

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

Выход 68.6%

Растворители

water

diethylene glycol monomethyl ether

water

Условия реакции

Обработка

1. 1
   ТемператураThe resulting mixture was cooled to room temperature
2. 2
   Экстракцияextracted with EtOAc (50 mL×3)
3. 3
   Сушкаdried over Na2SO4
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe residue was purified by column chromatography on silica gel (PE/EtOAc=1/1)

Методика

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.

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