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

HRID 1400905Notes

Reaction equation

HRID 1400905 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
100 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-eef4bc2510da43359eb3101a2a17614f
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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