Potassium Carbonate → 2-Phenylpyridine

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Reaktionsgleichung

Cl[C:2]1[C:7](CCC(O)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[C:13]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Pd(PPh3)4 (3.0 g, 2.6 mmol) was added to a solution of 2-chloro-3-carboxyethylpyridine (25 g, 134.7 mmol), phenylboronic acid (21.04 g, 172.6 mmol) and K2CO3 (55.1 g, 399 mmol) in 1,4-dioxane (200 mL) and water (200 mL). The reaction mixture was heated at 100° C. for 2 h. The solution was then cooled to room temperature and the dioxane was removed under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered through celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to get the 2-phenylpyridine derivative in 91% yield (27.98 g). LC-MS Rt (retention time): 2.45 min, MS: (ES) m/z 228 (M+H+).

Aufarbeitung

temperatureThe solution was then cooled to room temperature
customthe dioxane was removed under reduced pressure
extractionThe resulting aqueous layer was extracted with ethyl acetate
dry with materialthe combined organic layers were dried (Na2SO4)
filtrationfiltered through celite
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-7f1e12917c374963b11a21b22f3c90c9
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08906938B2

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