Potassium Carbonate → Ethyl 5-(4-chloro-3-methyl-[1,8]-naphthyridin-2-yl)pentanoate

Temperatur

75 °C

To a solution of ethyl 4-pentenoate (2.5 g, 20 mmol) in 60 mL THF was added 9-BBN (0.5 M in THF, 47 mL, 23 mmol) gradually at room temperature. After stirring for 10 hours, it was treated with Pd(OAc)2 (0.4 g, 2.0 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) (1.1 g, 2.0 mmol), K2CO3 (powder, 8.1 g, 58 mmol), 2,4-dichloro-3-methyl-naphthyridine (L) (3.6 g, 20 mmol) and 50 mL DMF. The reaction mixture was purged with argon for 5 minutes and then refluxed at 75° C. for 24 hours. It was cooled to room temperature and treated with 10 mL ethanolamine and stirred for 30 minutes. The mixture was diluted with 400 mL H2O and extracted with EtOAc(×3). The combined organic layers were washed with brine and dried. After solvent removal, the residue was purified by silica gel chromatography using EtOAc/hexanes (1:1) to give the desired product 3-3 as a liquid.

1. customThe reaction mixture was purged with argon for 5 minutes
2. temperatureIt was cooled to room temperature
3. additiontreated with 10 mL ethanolamine
4. stirringstirred for 30 minutes
5. additionThe mixture was diluted with 400 mL H2O
6. extractionextracted with EtOAc(×3)
7. washThe combined organic layers were washed with brine
8. customdried
9. customAfter solvent removal
10. customthe residue was purified by silica gel chromatography

ORD-Eintrag

ord-f61ba7ed573a42e384bb8cb7db67a911

Quelldatensatz

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06410526B1