Reaktion #40479

Reaktionsgleichung

6-chloro-7-fluoro-8-nitro-9H-β-carboline

sodium thioethoxide

H2O

→

6-chloro-7-ethylsulfanyl-8-nitro-9H-β-carboline

Ausbeute 81.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat RT
2. 2
   workup.ADDITIONadded drop-wise
3. 3
   SonstigeThe resulting precipitated solid
4. 4
   Filtrationwas collected by suction filtration
5. 5
   Waschenwashed with 1:1 hexanes/diethyl ether (2×20 ml)
6. 6
   Sonstigeair-dried

Vorschrift

A 25 ml round-bottom flask with a magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (102 mg, 0.38 mmol) in 5 ml of anhydrous DMF. To the resulting orange mixture at RT was slowly added sodium thioethoxide (80% pure, 69.7 mg, 0.66 mmol) in powder form. The reaction mixture was stirred at RT for 45 minutes, then added drop-wise to a 5:1 mixture of H2O/saturated sodium bicarbonate (˜30 ml). The resulting precipitated solid was collected by suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 95.0 mg of 6-chloro-7-ethylsulfanyl-8-nitro-9H-β-carboline as an orange solid (79%).

Quelle