Dichloromethane → 2-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181856
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([F:27])[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:28].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:27][C:21]1[CH:20]=[C:19]([S:16]([N:6]2[CH:5]([CH3:28])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=3)[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)(=[O:17])=[O:18])[CH:24]=[CH:23][C:22]=1[OH:25]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822898-Fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Produkt 1

HCID 103401602-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolAusbeute 82 %

Versuchsvorschrift

The title compound was prepared from 8-fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.50 g, 1.3 mmol), cyclohexene (2.3 mL, 22 mmol), and 1 M boron tribromide in dichloromethane (7.5 mL, 7.5 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), followed by trituration from hexane, to yield 2-fluoro-4-[(8-fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.40 g, 82%), m.p. 191° C.;

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-de0dd35684734f8ba9c093389222e50f
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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