Reaktion #76785

Reaktionsgleichung

sodium carbonate

5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

phenylboronic acid

1,2-dimethoxyethane

→

title compound

Ausbeute 68.5%

5′-Phenylspiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Ausbeute 68.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturunder reflux for 18 hours
3. 3
   SonstigeThe reaction mixture was then evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in chloroform (15 mL)
5. 5
   Waschenthe extract was washed with saturated aqueous sodium carbonate (5 mL)
6. 6
   ExtraktionThe aqueous layer was extracted with chloroform (2×15 mL)
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated under reduced pressure
10. 10
    SonstigePurification by flash chromatography through silica gel
11. 11
    Wascheneluting with ammoniated chloroform/methanol (95:5 to 9:1)

Vorschrift

Under a nitrogen atmosphere, 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (118 mg, 0.4 mmol), phenylboronic acid (54 mg, 0.443 mmol), and tetrakis(triphenylphosphine)palladium(0) (11 mg, 2.3 mol %) were stirred in a solution of 1,2-dimethoxyethane (3 mL) and ethanol (0.75 mL) containing 2M aqueous sodium carbonate (0.65 mL, 1.3 mmol). The mixture was heated under reflux for 18 hours. The reaction mixture was then evaporated under reduced pressure, the residue was dissolved in chloroform (15 mL), and the extract was washed with saturated aqueous sodium carbonate (5 mL). The aqueous layer was extracted with chloroform (2×15 mL), and the organic layers were combined, dried (MgSO4), filtered, and evaporated under reduced pressure. Purification by flash chromatography through silica gel, eluting with ammoniated chloroform/methanol (95:5 to 9:1), provided the title compound (80 mg, 0.274 mmol, 68%) as a tan solid: electrospray MS 293 ([MH]+, 100).

Quelle