Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181855
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH3:16])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[F:47][C:48]1[CH:49]=[C:50]([S:56](Cl)(=[O:58])=[O:57])[CH:51]=[CH:52][C:53]=1[O:54][CH3:55]>O1CCCC1.ClCCl>[CH:2]1[CH:15]=[CH:14][C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][CH2:5][C:4]=2[CH:3]=1.[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:56]([C:50]1[CH:51]=[CH:52][C:53]([O:54][CH3:55])=[C:48]([F:47])[CH:49]=1)(=[O:57])=[O:58])[CH:5]2[CH3:16]

Komponenten

10

Edukt 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 27745403-Fluoro-4-methoxybenzene-1-sulfonyl chlorideHCID 4311764Sodium borohydrideHCID 224823738-Fluoro-6-methylphenanthridine

Produkt 2

HCID 2199665,6-DihydrophenanthridineHCID 224822898-Fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The intermediate dihydrophenanthridine was prepared from 8-fluoro-6-methylphenanthridine, (Example 32, Method A, Step b, 2.00 g, 9.45 mmol), by treatment with sodium borohydride (1.79 g, 47.4 mmol) and trifluoroacetic acid (2.9 mL, 37.9 mmol) in tetrahydrofuran (38 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (2.7 mL, 19 mmol) and 3-fluoro-4-methoxybenzenesulfonyl chloride (0.78 g, 3.5 mmol, 1.1 equivalents) 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 re-crystallization from a mixture of ethyl acetate-hexane to yield 8-fluoro-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a homogeneous solid (1.08 g, 84% from the dihydrophenanthridine), m.p. 146-147° C.;

Aufarbeitung

  1. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d2d6e18ff5384c21be8b2410b19f82de
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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