Pyridine → HCID 59135753, Verbindung

HRID 2238968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238968
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[CH3:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22](Cl)(=[O:24])=[O:23].N1C=CC=C[CH:27]=1>>[CH3:27][N:1]([S:22]([C:18]1[N:17]([CH3:16])[CH:21]=[CH:20][N:19]=1)(=[O:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 116583831-Methyl-1H-imidazole-2-sulfonyl chloride

Produkt 1

HCID 59135753HCID 59135753, VerbindungAusbeute 59 %

Versuchsvorschrift

To a solution of ethyl 7-amino-1H-indole-2-carboxylate (3 g) in pyridine (30 mL) was added 1-methyl-1H-imidazole-2-sulfonyl chloride (3.6 g) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was dissolved in DMF (30 mL), potassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature, and the mixture was stirred for 3 hr at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (3.0 g, yield 59%) as white crystals from a fraction eluted with ethyl acetate:hexane=50:50. melting point 120° C.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe obtained residue was dissolved in DMF (30 mL)
  9. additionpotassium carbonate (2.1 g) and methyl iodide (2.1 g) were added at room temperature
  10. stirringthe mixture was stirred for 3 hr at room temperature
  11. additionWater was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with 1N hydrochloric acid, saturated brine and saturated aqueous sodium hydrogencarbonate solution
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b99fe0cf487743fea0cfbd6017e84193
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718798B2

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