Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181831
[CH3:1][O:2][C:3]1[C:4]2[C:13]([CH:14]=[CH:15][CH:16]=1)=[C:12]1[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]1)=[N:6][C:5]=2[CH3:17].[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:16]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.[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH:5]([CH3:17])[N:6]([S:56]([C:53]1[CH:52]=[CH:51][C:50]([O:49][CH3:48])=[CH:55][CH:54]=1)(=[O:58])=[O:57])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=12

Komponenten

10

Edukt 6

HCID 6422Trifluoroacetic acidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 224822867-Methoxy-6-methylphenanthridine

Produkt 2

HCID 2199665,6-DihydrophenanthridineHCID 224823397-Methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The intermediate dihydrophenanthridine was prepared from 7-methoxy-6-methylphenanthridine, (Example 36, Step b, 0.61 g, 2.7 mmol), by treatement with sodium borohydride (0.62 g, 16 mmol) and trifluoroacetic acid (0.84 mL, 10.8 mmol) in tetrahydrofuran (12 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (0.77 mL, 5.5 mmol) and 4-methoxybenzenesulfonyl chloride (0.57 g, 2.8 mmol, 2 equivalents) in dichloromethane (3 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 1:4 gradient), to yield 7-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a white solid (0.17 g, 33% from the dihydrophenanthridine);

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 1:4 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-1e307605e93a432c9d2ae43a1ed37840
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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