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

HRID 2106018
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2106018
Br[C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:7]=1.[F-].[K+].[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:27][C:10]([C:23]([F:26])([F:25])[F:24])([CH2:9][C:8]([C:6]1[CH:7]=[C:2]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:3]=[CH:4][C:5]=1[O:30][CH3:31])([CH3:29])[CH3:28])[CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH:14]=[CH:13]1
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Komponenten

6

Edukt 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 578097571-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Produkt 1

HCID 578097641-[2-hydroxy-4-(4-methoxybiphenyl-3-yl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 22635083Tetrahydrofuran tolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-35bcc51e6d964061b53a613272ba5d26
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07579469B2

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