Hydrochloric Acid → Methyl 4-(4-amino-6-methoxyquinolin-2-yl)benzoate

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.

1. temperatureThe mixture was cooled
2. extractionextracted with EtOAc (80 mL×3)
3. washThe combined organic layers were washed with brine (150 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated in vacuo
6. washThe residue was washed with EtOAc (50 mL)
7. filtrationthe mixture was filtered
8. concentrationthen concentrated

ORD-Eintrag

ord-cc115375d5d94fefb8a755343c3e4afc

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09433618B2