반응 #84103

반응 방정식

HCl

Intermediate 8

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

4-methoxycarbonylphenylboronic acid

K2CO3

DMF

→

product

수율 46.0%

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

수율 46.0%

용매

H2O

반응 조건

후처리

1. 1
   온도The mixture was cooled
2. 2
   추출extracted with EtOAc (80 mL×3)
3. 3
   세척The combined organic layers were washed with brine (150 mL)
4. 4
   건조dried over anhydrous Na2SO4
5. 5
   농축concentrated in vacuo
6. 6
   세척The residue was washed with EtOAc (50 mL)
7. 7
   여과the mixture was filtered
8. 8
   농축then concentrated

실험 절차

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.

출처