Phenylboronic Acid → 1-[2-hydroxy-4-(4-methoxybiphenyl-3-yl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

A mixture of 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (200 mg, 0.4 mmol), Pd(OAc)2 (9 mg, 0.04 mmol), DCyBPP ((2-dicyclohexylphosphino)biphenyl, 28 mg, 0.08 mmol), KF (93 mg, 1.6 mmol) in toluene/THF (3/2 mL) at room temperature was treated with phenylboronic acid (98 mg, 0.8 mmol). The reaction mixture stirred overnight at room temperature and filtered through CELITE® filter aid. The residue was diluted with EtOAc (20 mL), washed with aqueous NaOH (11.0M, 10 mL), water, and brine (10 mL). The organic phase was dried over sodium sulfate, filtered, and solvent was evaporated in vacuo. The residue was purified silica gel chromatography and then by reverse phase HPLC to provide 1-[2-hydroxy-4-(4-methoxybiphenyl-3-yl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one as white solid.

1. filtrationfiltered through CELITE®
2. filtrationfilter aid
3. additionThe residue was diluted with EtOAc (20 mL)
4. washwashed with aqueous NaOH (11.0M, 10 mL), water, and brine (10 mL)
5. dry with materialThe organic phase was dried over sodium sulfate
6. filtrationfiltered
7. customsolvent was evaporated in vacuo
8. customThe residue was purified silica gel chromatography

ORD 기록

ord-35bcc51e6d964061b53a613272ba5d26

출처 데이터셋

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07579469B2