Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181848
[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.[Cl:48][C:49]1[CH:50]=[C:51]([S:57](Cl)(=[O:59])=[O:58])[CH:52]=[CH:53][C:54]=1[O:55][CH3:56]>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:57]([C:51]1[CH:52]=[CH:53][C:54]([O:55][CH3:56])=[C:49]([Cl:48])[CH:50]=1)(=[O:58])=[O:59])[CH3:2]

Komponenten

10

Edukt 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideHCID 22482260HCID 22482260, Verbindung

Produkt 2

HCID 2199665,6-DihydrophenanthridineHCID 22482342HCID 22482342, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The intermediate dihydrophenanthridine was prepared from 6-ethyl-8-fluorophenanthridine, (Example 40, Step b, 0.40 g, 1.8 mmol), by treatment with sodium borohydride (0.40 g, 10.6 mmol) and trifluoroacetic acid (0.55 mL, 7.1 mmol) in tetrahydrofuran (7 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.9 mL, 6.4 mmol) and 3-chloro-4-methoxybenzenesulfonyl chloride (0.51 g, 2.1 mmol, 2.1 equivalents) in dichloromethane (5 mL), according to the procedure and in the same manner as described in Example 32, Method A, Step d, to afford 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine as a crude product, which was utilized without further purification.

Quellen und Nachweise

ORD-Eintrag
ord-1afc60d4b4184dada63199b24b44fd26
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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