Potassium Carbonate → 2-Phenylpyridine

HRID 2273858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273858
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

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866427913-(2-chloropyridin-3-yl)propanoic acid

Produkt 1

HCID 138872-PhenylpyridineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

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

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

Quellen und Nachweise

ORD-Eintrag
ord-af4d1ebb8393435b9a13017406a7cfa0
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126939B2

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