Réaction #76785

Équation de réaction

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

Rendement 68.5%

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

Rendement 68.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureunder reflux for 18 hours
3. 3
   AutreThe reaction mixture was then evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in chloroform (15 mL)
5. 5
   Lavagethe extract was washed with saturated aqueous sodium carbonate (5 mL)
6. 6
   ExtractionThe aqueous layer was extracted with chloroform (2×15 mL)
7. 7
   Séchagedried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated under reduced pressure
10. 10
    AutrePurification by flash chromatography through silica gel
11. 11
    Lavageeluting with ammoniated chloroform/methanol (95:5 to 9:1)

Mode opératoire

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).

Source