반응 #716039

반응 방정식

2-chloro-6-methoxyquinoline

Intermediate 1

2-chloro-6-methoxyquinoline

4-carboxy-2-chlorophenylboronic acid

K2CO3

→

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

수율 46.0%

용매

EtOAc

DEGME H2O

반응 조건

후처리

1. 1
   기타was degassed three times under N2 atmosphere
2. 2
   여과filtered
3. 3
   세척The filtrate was washed with brine (20 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

A mixture of 2-chloro-6-methoxyquinoline (Intermediate 1) (200 mg, 1.04 mmol), 4-carboxy-2-chlorophenylboronic acid (247 mg, 1.24 mmol) and K2CO3 (369 mg, 2.70 mmol) in DEGME/H2O (7.0 mL/2.0 mL) was degassed three times under N2 atmosphere. Then PdCl2(dppf) (75 mg, 0.104 mmol) was added and the mixture was heated to 110° C. for 3 hours under N2 atmosphere. The reaction mixture was diluted with EtOAc (100 mL) and filtered. The filtrate was washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to give 3-chloro-4-(6-methoxyquinolin-2-yl)benzoic acid (150 mg, yield 46%) as a yellow solid, which was used for the next step without further purification.

출처