Dichloromethane → 4-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181861
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:2].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:23]([C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH3:2]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482332HCID 22482332, Verbindung

Produkt 1

HCID 103672334-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenolAusbeute 63 %

Versuchsvorschrift

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-thien-3-yl-5,6-dihydrophenanthridine (0.28 g, 0.58 mmol), cyclohexene (13 mL, 10.5 mmol), and 1 M boron tribromide in dichloromethane (3.5 mL, 3.5 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield 4-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.17 g, 63%);

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-e4e965c295c34c54abc331cbb14add7f
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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