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

HRID 355815노트

반응식

HRID 355815 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  1. customThe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-c1ce26c108844caabe0638530b20cdfb
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834482

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