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

HRID 1400905ノート

反応式

HRID 1400905 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-eef4bc2510da43359eb3101a2a17614f
出典データセット
uspto-grants-2014_12
特許番号
US08906852B2

反応ノート

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