Reaktion #76784

Reaktionsgleichung

sodium carbonate

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

sodium acetate

Bromine

→

title compound

Ausbeute 81.0%

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

Ausbeute 81.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was then heated
2. 2
   Temperaturunder reflux for 1 hour
3. 3
   Extraktionextracted with chloroform (3×15 mL)
4. 4
   TrocknenThe combined extracts were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under reduced pressure

Vorschrift

A solution of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (100 mg, 0.462 mmol) and sodium acetate (410 mg, 5 mmol) in 50% aqueous acetic acid (4 mL) was heated to 60° C. Bromine (0.100 mL, 1.94 mmol) was added via a syringe over 10 minutes, and the solution was then heated under reflux for 1 hour. The mixture was allowed to cool to ambient temperature, basified to pH>10 with sodium carbonate, and extracted with chloroform (3×15 mL). The combined extracts were dried (MgSO4), filtered, and evaporated under reduced pressure to give the title compound (110 mg, 0.37 mmol, 81%) as an off-white solid: electrospray MS 295 ([MH]+, with 79Br, 100), 297 ([MH]+, with 81Br, 98).

Quelle