Dichloromethane → HCID 22482332, Verbindung

HRID 2181860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181860
Br[C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=3)[C:4]=2[CH:3]=1.[S:30]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31]1.ClCCl.[OH-].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:27]([CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=2)[C:4]2[CH:3]=[C:2]([C:32]3[CH:33]=[CH:34][S:30][CH:31]=3)[CH:15]=[CH:14][C:13]=2[N:12]1[S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)(=[O:17])=[O:18])[CH3:28]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 581760Thiophene-3-boronic acidHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Produkt 1

HCID 22482332HCID 22482332, VerbindungAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Versuchsvorschrift

The title compound was prepared from 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.35 g, 0.73 mmol), 3-thiopheneboronic acid (0.09 g, 0.73 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.02 g, 0.02 mmol), and a 5 N aqueous sodium hydroxide solution (0.3 mL, 1.5 mmol) according to the procedure and in the same manner as described in Example 47, Step a. The crude material was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-thien-3-yl-5,6-dihydrophenanthridine as a solid (0.18 g, 51%);

Aufarbeitung

  1. customThe crude material was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-84a77b5d7397499d8d320a6cb52c03ff
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

Notizen zur Reaktion

Wird geladen…