반응 #76785

반응 방정식

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

수율 68.5%

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

수율 68.5%

용매

ethanol

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도under reflux for 18 hours
3. 3
   기타The reaction mixture was then evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in chloroform (15 mL)
5. 5
   세척the extract was washed with saturated aqueous sodium carbonate (5 mL)
6. 6
   추출The aqueous layer was extracted with chloroform (2×15 mL)
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   기타evaporated under reduced pressure
10. 10
    기타Purification by flash chromatography through silica gel
11. 11
    세척eluting with ammoniated chloroform/methanol (95:5 to 9:1)

실험 절차

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).

출처