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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 532639Erstellt: 25. Oktober 2026

Sodium Carbonate → 6-(4-Methoxy-phenyl)-2-pyridin-4-yl-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

https://huagongshe.com/reaction/532639

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium CarbonateHCID 10340—
Edukt4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 2734648—
Edukt2-Bromo-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneHCID 86699230—
KatalysatorHCID 178418476HCID 178418476—
LösungsmittelToluene ethanolHCID 21863594—
Produkt6-(4-Methoxy-phenyl)-2-pyridin-4-yl-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneHCID 8669923365%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A mixture of the corresponding 2-Bromo-6-(4-methoxy-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.76 g, 1.5 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (0.3 g, 2.3 mmol), Na2CO3 (2 M, 3.7 mL), and Pd(PPh3)2Cl2 (14.6 mg, 0.012 mmol) in toluene/ethanol (1:1, 10 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 (20% EtOAc in hexane) to give 6-(4-Methoxy-phenyl)-2-pyridin-4-yl-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene as brown solid in 65% yield.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08853207B2
Quelldatensatzuspto-grants-2014_10
ORD IDord-a316e09be7c94aba93a5628c73621c8f
Quellennotizuspto-grants-2014_10