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

Temperature

0 °C

At 0° C., NaH (60 percent, 0.48 g, 12.0 mmol) was added to a THF solution (15 mL) containing 6-(4-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (3.1 g, 9.7 mmol). Then SEM-Cl (90% pure, 2.4 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-(4-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 69% 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 record

ord-58bc75002d2f472c9a6e3c4297efec02

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853207B2