Sodium hydride → HCID 86699222, Verbindung

At 0° C., NaH (60 percent, 0.6 g, 12.0 mmol) was added to a THF solution (15 mL) containing 6-(3-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (3.1 g, 9.7 mmol). Then SEM-Cl (2.5 mL, 12 mmol) was added to the reaction mixture and the resulting mixture was stirred at 0° C. for 30 min, warmed up to 80° C. and stirred for 2 hr. The solution was cooled to room temperature and poured into ice water. The resulting mixture was extracted with ethyl acetate. The organic layer was collected and washed with saturated aqueous NH4Cl, dried over MgSO4(s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (20% EtOAc in hexane) to give 6-(3-Bromo-phenyl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (3.0 g, 6.7 mmol) as brown solid in 70% yield.

1. temperaturewarmed up to 80° C.
2. stirringstirred for 2 hr
3. temperatureThe solution was cooled to room temperature
4. extractionThe resulting mixture was extracted with ethyl acetate
5. customThe organic layer was collected
6. washwashed with saturated aqueous NH4Cl
7. dry with materialdried over MgSO4(s)
8. concentrationconcentrated under reduced pressure
9. customThe oily residue was purified by gravity column chromatography (20% EtOAc in hexane)

ORD-Eintrag

ord-0c14dabf208c42a386f9137fe383e61f

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853207B2