Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181834
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10](=[C:11]3[C:16]=1[CH:15]=[C:14]([F:17])[CH:13]=[CH:12]3)[CH:9]=[CH:8][CH:7]=[CH:6]2)[CH3:2].[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][CH:51]=1>O1CCCC1.ClCCl>[CH:14]1[CH:13]=[CH:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[NH:4][CH2:3][C:16]=2[CH:15]=1.[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]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:56]([C:53]1[CH:52]=[CH:51][C:50]([O:49][CH3:48])=[CH:55][CH:54]=1)(=[O:58])=[O:57])[CH3:2]

Komponenten

10

Edukt 6

HCID 6422Trifluoroacetic acidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 22482260HCID 22482260, Verbindung

Produkt 2

HCID 2199665,6-DihydrophenanthridineHCID 224823306-Ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The intermediate dihydrophenanthridine was prepared from 6-ethyl-8-fluorophenanthridine (1.10 g, 4.88 mmol) by treatment with sodium borohydride (1.11 g, 29.3 mmol) and trifluoroacetic acid (1.50 mL, 19.5 mmol) in tetrahydrofuran (18 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (4.1 mL, 29.3 mmol) and 4-methoxybenzenesulfonyl chloride (1.11 g, 5.37 mmol) in dichloromethane (5 mL) according to the procedure and in the same manner as described in Example 32, Method A, Step d. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 3:7 gradient), to yield 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a homogeneous, white, crystalline, solid (1.67 g, 87%), m.p. 153-156° C.;

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 3:7 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0d3d0ec642534bc9b2cc3186bd9e33c4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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