Cesium carbonate → 6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

HRID 33517

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>CN(C)C=O.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]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:26][CH:25]=2)[N:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

162 mg (0.14 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 2.0 g (9.25 mmol) methyl-6-bromo-pyridine-2-carboxylate in 46 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 4.52 g (13.9 mmol) cesium carbonate and 2.1 g (10.18 mmol) of 4-(trifluoromethoxy)phenylboronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.23 g (39%) of 6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
customthe filtrate evaporated
washwashed twice with water
dry with materialdried over sodium sulphate
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-3228abf9434f47c796b1731712ce4c8b
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07429605B2

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