Reaktion #721725

Reaktionsgleichung

ethyl 3-((6-chloro-3′-fluoro-[2,2′-bipyridin]-3-yl)thio)propanoate

potassium 2-methylpropan-2-olate

→

2-chlorothieno[3,2-b:4,5-b′]dipyridine

Ausbeute 68.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegassed with nitrogen for 10 minutes
2. 2
   Temperaturheated
3. 3
   SonstigeThe reaction was quenched with aqueous ammonium chloride
4. 4
   Extraktionextracted 2× with EtOAc
5. 5
   SonstigeThe crude product was purified by column chromatography

Vorschrift

A 500 mL RBF was charged with ethyl 3-((6-chloro-3′-fluoro-[2,2′-bipyridin]-3-yl)thio)propanoate (16.55 g, 48.6 mmol), THF (Volume: 194 mL) and degassed with nitrogen for 10 minutes, then treated with potassium 2-methylpropan-2-olate (8.17 g, 72.8 mmol) and heated to reflux at 75° C. for 24 hours. The reaction was quenched with aqueous ammonium chloride, extracted 2× with EtOAc. The crude product was purified by column chromatography to give 2-chlorothieno[3,2-b:4,5-b′]dipyridine (7 g, 68% yield).

Quelle