Reaktion #619745

Reaktionsgleichung

6-(4-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

3,4-Dimethoxyphenylboronic acid

Na2CO3

→

6-(3′,4′-Dimethoxy-biphenyl-4-yl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Ausbeute 68.0%

Lösungsmittel

toluene ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   SonstigeThe target product was purified by gravity column chromatography (50% EtOAc in hexane)

Vorschrift

A mixture of the corresponding intermediate 6-(4-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.3 g, 0.9 mmol), 3,4-Dimethoxyphenylboronic acid (0.276 g, 1.5 mmol), Na2CO3 (2 M, 2.5 mL), and Pd(PPh3)2Cl2 (87 mg, 0.7 mmol) in toluene/ethanol (1:1, 6 mL) was heated at 100° C. for 8 hr. The solution was cooled to room temperature and extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give 6-(3′,4′-Dimethoxy-biphenyl-4-yl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene as brown solid in 68% yield.

Quelle