Triphenylphosphine → 9-chloro-5-ethyl-5H-phenanthridin-6-one

Temperatur

23 °C

Palladium acetate (466 mg, 2.07 mol) was added to a suspension of silver carbonate (5.7 g, 20.7 mmol), triphenylphosphine (1.08 g, 4.15 mmol), and 4-chloro-N-ethyl-2-iodo-N-phenyl-benzamide I-14a (4.0 g, 10.4 mmol) in acetonitrile (52 ml). The reaction mixture was heated to reflux for 1 hour and cooled to 23° C. The mixture was filtered through a plug of celite and the filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml). The combined filtrates were washed with saturated sodium chloride (50 ml), dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane) to afford 9-Chloro-5-ethyl-5H-phenanthridin-6-one I-14b (1.68 g, 63%) as a yellow solid.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 1 hour
3. filtrationThe mixture was filtered through a plug of celite
4. washthe filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml)
5. washThe combined filtrates were washed with saturated sodium chloride (50 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane)

ORD-Eintrag

ord-03d06a9bc6054e8f8fda475171888702

Quelldatensatz

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06958347B2