Water → 2-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine

HRID 2179996Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O.Cl[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

2-methoxy-4-trifluoromethoxybenzene boronic acid (72 g, 0.31 mol), K2CO3 (80.16 g, 0.58 mol) and water (100 ml) are added to a solution of 2-chloro-3-methyl -5-nitro-pyridine (50 g, 0.29 mol) in DME (500 ml) at room temperature. Pd(Ph3P)4 (3.35 g, 2.9 mmol) is added and the mixture is stirred at 85° C. for 19 hours. 500 ml of water is added and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. After removal of the solvent under reduced pressure, the residue is purified by flash column chromatography (hexane/EtOAc 9:1) to obtain 2-(2-methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine. Rf (hexane/EtOAc=9:1)=0.41.

Aufarbeitung

extractionthe mixture is extracted with EtOAc
washThe combined extracts are washed with brine
dry with materialdried over Na2SO4
customAfter removal of the solvent under reduced pressure
customthe residue is purified by flash column chromatography (hexane/EtOAc 9:1)

Quellen und Nachweise

ORD-Eintrag: ord-314049de7972427d9e1f92cd737a6b08
Quelldatensatz: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06887875B2

Notizen zur Reaktion

Wird geladen…