2-Pyrrolidone → 1-(2-(6-Bromopyridin-3-yl)ethyl)pyrrolidin-2-one

HRID 1400905노트

반응식

HRID 1400905 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]Br)=[CH:4][N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].[H-].[Na+]>CO.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH2:9][N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 584744292-Bromo-5-(2-bromoethyl)pyridine

생성물 1

HCID 584748611-(2-(6-Bromopyridin-3-yl)ethyl)pyrrolidin-2-one수율 75.5%

시약·촉매·용매 1

HCID 21584119Ethylacetate methanol용매

반응 조건

온도
100 °C

실험 절차

To a mixture of dibromide 290 (1.7 g, 6.4 mmol) in 2-pyrrolidone (10 mL, 130 mmol) at room temperature was added sodium hydride, 40% dispersion in mineral oil (1.16 g, 19.3 mmol). This reaction mixture was then heated to 100° C. for 2 h, then cooled to RT and partitioned between water and ethyl acetate. The organic phase was collected, washed with water, saturated aqueous ammonium chloride, and brine. It was then dried (anhydrous MgSO4), filtered and concentrated. Silica gel chromatography (10% methanol/ethyl acetate) gave title compound 291 (1.3 g, 75% yield) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.17-8.16 (m, 1H); 7.42-7.37 (m, 2H); 3.49 (t, J=7.4, 2H); 3.28 (t, J=6.9, 2H); 2.79 (t, J=7.2, 2H); 2.30 (t, J=7.8, 2H); 1.95 (quintet, 7.6, 2H). MS (M+H): 269.1, 271.1

후처리

  1. temperaturecooled to RT
  2. custompartitioned between water and ethyl acetate
  3. customThe organic phase was collected
  4. washwashed with water, saturated aqueous ammonium chloride, and brine
  5. dry with materialIt was then dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eef4bc2510da43359eb3101a2a17614f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906852B2

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