Dichloromethane → 2-(3-(Difluoromethyl)phenyl)quinoline-8-carboxylic acid

HRID 2359407

Reaktionsgleichung

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:15][CH:16]([F:32])[C:17]1[CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:21][CH:22]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:15][CH:16]([F:32])[C:17]1[CH:22]=[C:21]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:20]=[CH:19][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a solution of 2-chloroquinoline-8-carboxylic acid (3.1 g, 15.0 mmol) in DME (20 mL) and water (2 mL) was added 2-(3-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.5 g, 17.7 mmol), K3PO4 (5.2 g, 22.6 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.50 g, 0.63 mmol). The reaction mixture was stirred under nitrogen at 85° C. for 12 hours, then the reaction was cooled to room temperature and water (20 mL) was added. The mixture was filtered and the filter cake was washed with water, and the solid was dried in vacuo to give 2-(3-(difluoromethyl)phenyl)quinoline-8-carboxylic acid (3.6 g, 80% yield).

Aufarbeitung

temperaturethe reaction was cooled to room temperature
filtrationThe mixture was filtered
washthe filter cake was washed with water
customthe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-fdda792a98ee4617a9e93bf47d884ed2
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08685970B2

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