Cyclohexene → 3-[(3,9-Difluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181913
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[C:8]([F:28])[CH:7]=3.C1CCCCC=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[C:8]([F:28])[CH:7]=3

Komponenten

5

Edukt 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224823263,9-Difluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Produkt 1

HCID 224823143-[(3,9-Difluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared from 3,9-difluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (150 mg, 0.37 mmol), cyclohexene (757 μL, 7.5 mmol), and 1.0 M solution of boron tribromide in dichloromethane (2.24 mL) according to the procedure and in the same manner as described in Example 105, step e. The volatile components were removed in vacuo, and the crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 5%-50% methyl tert-butyl ether in hexane, to afford the product (98 mg, 78%) as a solid, m.p. 167.2-173° C.;

Aufarbeitung

  1. customThe volatile components were removed in vacuo
  2. customthe crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  3. washeluting with a gradient of 5%-50% methyl tert-butyl ether in hexane

Quellen und Nachweise

ORD-Eintrag
ord-32de366ab2a347afbee1827b2a7ef4a4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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