Ammonium Chloride → HCID 22465395, Verbindung

HRID 1936313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1936313
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.[Li].CON(C)[C:25]([C:27]1[S:28][C:29]([Cl:32])=[CH:30][CH:31]=1)=[O:26].[Cl-].[NH4+]>C1COCC1>[Cl:20][C:16]1[CH:15]=[C:14]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:25]([C:27]4[S:28][C:29]([Cl:32])=[CH:30][CH:31]=4)=[O:26])[CH:3]=3)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 120166726-Bromo-4-(3-chlorophenyl)-2-methoxyquinolineHCID 60644866HCID 60644866, Verbindung

Produkt 1

HCID 22465395HCID 22465395, VerbindungAusbeute 46,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 6-bromo-4-(3-chloro-phenyl)-2-methoxy-quinoline (500 mg, 1.43 mmol) in THF (2 ml) was added n-buthyl lithium (2.5 M in hexane, 0.63 ml, 1.58 mmol) dropwise at −78° C. under an atmosphere of dry N2. After stirring at −78° C. for 30 minutes, a solution of 5-chloro-thiophene-2-carboxylic acid methoxy-methyl-amide (440 mg, 2.15 mmol) in THF (1 ml) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 15 hours. To the mixture was added a saturated aqueous solution of ammonium chloride at 0° C. THF was removed from the resulting heterogeneous solution. The aqueous mixture was extracted with chloroform (CHCl3). The organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to yield the crude product. It was chromatographed on silica gel with MeOH-CHCl3NH4OH (2:98:0.2 to 5:95:0.5) as eluents to afford the title compound of example 40A (273.5 mg, 46% yield).

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 15 hours
  3. customTHF was removed from the resulting heterogeneous solution
  4. extractionThe aqueous mixture was extracted with chloroform (CHCl3)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customto yield the crude product
  9. customIt was chromatographed on silica gel with MeOH-CHCl3NH4OH (2:98:0.2 to 5:95:0.5) as eluents

Quellen und Nachweise

ORD-Eintrag
ord-5939d3c532e34a67ae5c24b30ec16de4
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06388092B2

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