Reaktion #2269032

Reaktionsgleichung

2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

phenylboronic acid

dichloromethane

sodium hydroxide

→

title compound

Ausbeute 52.8%

6-Ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-phenyl-5,6-dihydrophenanthridine

Ausbeute 52.8%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux for twelve hours
3. 3
   Sonstigequenched with a saturated, aqueous, sodium chloride solution (10 mL) and diethyl ether (50 mL)
4. 4
   TrocknenThe separated organic phase was dried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo to a crude product
7. 7
   SonstigeThe crude product was purified by flash column chromatography on silica gel
8. 8
   Wascheneluting with a mixture of ethyl acetate-hexane (1:4)

Vorschrift

A stirred solution of 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.25 g, 0.52 mmol) and phenylboronic acid (0.06 g, 0.52 mmol) in tetrahydrofuran (5 mL) was treated under nitrogen with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.01 g, 0.02 mmol) and a 5 N aqueous sodium hydroxide solution (0.2 mL, 1 mmol). The reaction mixture was heated at reflux for twelve hours, cooled to room temperature, and quenched with a saturated, aqueous, sodium chloride solution (10 mL) and diethyl ether (50 mL). The separated organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to a crude product. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield the title compound as a solid (0.13 g, 50%);

Quelle