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

HRID 355815Notes

Reaction equation

HRID 355815 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 110678029-(3-Chloro-1-propyl)-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-9H-beta-carbolineYield 166.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-c1ce26c108844caabe0638530b20cdfb
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

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