4,7-Dichloroquinoline → 7-chloro-4-(5-fluoro-2-methyl-1H-indol-3-yl)-quinoline

HRID 418441

Reaktionsgleichung

Reaktionsgleichung von HRID 418441
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>CN1C(=O)CCC1.Cl.O1CCOCC1>[Cl:23][C:19]1[CH:18]=[C:17]2[C:22]([C:13]([C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]=3[CH3:11])=[CH:14][CH:15]=[N:16]2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 2

HCID 68664,7-DichloroquinolineHCID 27787155-Fluoro-2-methylindole

Produkt 1

HCID 684581957-chloro-4-(5-fluoro-2-methyl-1H-indol-3-yl)-quinolineAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 5-fluoro-2-methylindole (149 mg) and 4,7-dichloroquinoline (198 mg) in NMP (2 ml) and 4M hydrogen chloride in dioxan (0.2 ml) was stirred at 140° C. overnight and then at 150° C. for 1 h. and evaporated. The residue was taken up in ethyl acetate, washed with brine (3×), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica chromatography using acetone/isohexane (2:8) as eluent to give the sub-title compound (250 mg).

Aufarbeitung

  1. customevaporated
  2. washwashed with brine (3×)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fb62c8b020ba418e8f05ec14c5a0d741
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093278B2

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