1-Bromo-3-chloropropane → 9-(3-Chloro-1-propyl)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carboline

HRID 355815

Reaktionsgleichung

Reaktionsgleichung von HRID 355815
[CH2:1]([C:3]1[N:7]=[C:6]([C:8]2[N:9]=[CH:10][C:11]3[NH:12][C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[O:5][N:4]=1)[CH3:2].[H-].[Na+].[H][H].Br[CH2:26][CH2:27][CH2:28][Cl:29]>CN(C=O)C>[Cl:29][CH2:28][CH2:27][CH2:26][N:12]1[C:11]2[CH:10]=[N:9][C:8]([C:6]3[O:5][N:4]=[C:3]([CH2:1][CH3:2])[N:7]=3)=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Komponenten

6

Edukt 4

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 189407053-(3-Ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 110678029-(3-Chloro-1-propyl)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineAusbeute 166,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of Compound 2 (0.73 g, 2.8 mmol) in anhydrous DMF (100 mL), sodium hydride (60% in mineral oil, 0.13 g, 3.3 mmol) was carefully added. The resulting mixture was stirred at room temperature for 30 min, until hydrogen evolution had ceased. The reaction mixture was slowly added to a solution of 1-bromo-3-chloropropane (0.52 g, 3.3 mmol) in anhydrous DMF (150 mL). The resulting mixture was stirred at room temperature for 12 h. The solvents were removed in vacuo to give a yellow solid (1.59 g). The residue was dissolved in acetone, filtered and the filtrate concentrated in vacuo, giving the title compound (1.07 g, 100%). 1H- and 13 C-NMR revealed that the crude product was a mixture of the bromo and chloro isomers in the ratio 70:8. The crude product was used without further purification.

Aufarbeitung

  1. customThe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c1ce26c108844caabe0638530b20cdfb
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834482

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