Sodium Carbonate → 3-(Pyridin-3-yl)cyclohex-2-en-1-one
Reaktionsgleichung
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)[CH:10]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium-DCM complex (313 mg, 0.383 mmol) was added to a stirred mixture of 8a (500 mg, 3.83 mmol), pyridin-3-yl-boronic acid (565 mg, 4.60 mmol) and sodium carbonate (2.87 mL of a 2M aq. solution, 5.74 mmol) in dioxane (14.0 mL) and water (2.00 mL). The resulting mixture was degassed and heated to 95° C. After 7 h, the reaction mixture was cooled to rt, diluted with EtOAc, filtered through a short column of Celite®, eluting copiously with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent) to afford the title compound, 8b. m/z (ES) 174 (MH)+
Aufarbeitung
- customThe resulting mixture was degassed
- temperaturethe reaction mixture was cooled to rt
- additiondiluted with EtOAc
- filtrationfiltered through a short column of Celite®
- washeluting copiously with EtOAc
- washThe organics were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by column chromatography on silica gel (0-90% EtOAc/hexanes as eluent)
Quellen und Nachweise
- ORD-Eintrag
- ord-a8cb637dc19e429d8fb295052318e14f
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029377B2
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