5-Methoxy-2-methylindole → Quinoline,4-(5-methoxy-2-methyl-1h-indol-3-yl)-8-methyl-

HRID 418440

Reaktionsgleichung

Reaktionsgleichung von HRID 418440
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.Cl[C:14]1[C:23]2[C:18](=[C:19]([C:24](F)(F)F)[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1.Cl.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:14]1[C:23]2[C:18](=[C:19]([CH3:24])[CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 3

HCID 706425-Methoxy-2-methylindoleHCID 902624-Chloro-8-(trifluoromethyl)quinolineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 66651927Quinoline,4-(5-methoxy-2-methyl-1h-indol-3-yl)-8-methyl-Ausbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 5-methoxy-2-methylindole (346 mg) and 4-chloro-8-trifluoromethylquinoline (380 mg) in NMP (1 ml) and 4M HCl in dioxane (0.1 ml) was heated at 140° C. for 50 min. Aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organic extracts were dried (MgSO4), evaporated and purified by chromatography (silica, petrol-acetone as eluent) to give the sub-title compound (465 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated
  4. custompurified by chromatography (silica, petrol-acetone as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-1212322d85cc4dc092eb8ba137401bee
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093278B2

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