2-Pyrrolidone → HCID 86679117, compound

HRID 1774738Notes

Reaction equation

HRID 1774738 reaction equation
[H-].[Na+].[NH:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([CH2:16]Cl)[CH:15]=1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([CH2:16][N:3]2[CH2:7][CH2:6][CH2:5][C:4]2=[O:8])[CH:13]=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 86679117HCID 86679117, compoundYield 117%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 0.044 g, 1.09 mmol) in DMF (2 mL) was added pyrrolidin-2-one (0.081 g, 0.945 mmol) and the reaction mixture was stirred at room temperature for 20 min. Then, 3-bromo-5-chloromethyl-pyridine (0.15 g, 0.727 mmol) was added and the resulting suspension was heated at 60° C. over night. The mixture was quenched with water (2 mL) and extracted with EtOAc (2×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.217 g, 87%) as a white solid. MS: 251.1, 257.1 (M+H+).

Workup

  1. temperaturethe resulting suspension was heated at 60° C. over night
  2. customThe mixture was quenched with water (2 mL)
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-09b1ae3ba8c644d1933525c1ef093013
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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