Реакция #84103

Уравнение реакции

HCl

Intermediate 8

3-chloro-4-(6-hydroxyquinolin-2-yl)benzoic acid

4-methoxycarbonylphenylboronic acid

K2CO3

DMF

→

product

Выход 46.0%

methyl 4-(4-amino-6-methoxyquinolin-2-yl)benzoate

Выход 46.0%

Растворители

H2O

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled
2. 2
   Экстракцияextracted with EtOAc (80 mL×3)
3. 3
   ПромывкаThe combined organic layers were washed with brine (150 mL)
4. 4
   Сушкаdried over anhydrous Na2SO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ПромывкаThe residue was washed with EtOAc (50 mL)
7. 7
   Фильтрацияthe mixture was filtered
8. 8
   Концентрированиеthen concentrated

Методика

A mixture solution of Intermediate 8 (4.70 g, 22.5 mmol), 4-methoxycarbonylphenylboronic acid (4.01 g, 22.5 mmol), K2CO3 (6.53 g, 47.2 mmol), Pd(dppf)Cl2 (470 mg, 0.407 mmol) in DMF (20 mL) and H2O (4 mL) was stirred under N2 atmosphere at 130° C. for 5 hours. The mixture was cooled, acidified with aqueous HCl (1M) until pH=6 and extracted with EtOAc (80 mL×3). The combined organic layers were washed with brine (150 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was washed with EtOAc (50 mL), the mixture was filtered then concentrated to give the product (3.20 g, yield 46%) as an off-white solid.

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