Water → HCID 67997446, compound

HRID 1425999Notes

Reaction equation

HRID 1425999 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11]2=[O:16])=[N:8][CH:9]=1.[CH3:17]I.O>CN(C)C=O.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH3:17])[CH2:14][CH2:13][N:12]([CH3:15])[C:11]2=[O:16])=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 679978423-(5-Bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one

Product 1

HCID 67997446HCID 67997446, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (55% in mineral oil, 0.17 g) was added to a solution of 3-(5-bromo-pyridin-2-yl)-1-methyl-pyrrolidin-2-one (0.77 g) and methyl iodide (0.44 mL) in N,N-dimethylformamide (15 mL) in argon atmosphere at room temperature. The resulting mixture was stirred at room temperature overnight. Water and ethyl acetate were then added and the organic phase of the resulting mixture was separated. The organic phase was washed with brine, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (dichloro-methane/ethyl acetate 1:1) to give the title compound as a colorless oil. Yield: 0.50 g (61% of theory); LC (method 1): tR=1.60 min; Mass spectrum (ESI+): m/z=269/271 (Br) [M+H]+.

Workup

  1. customthe organic phase of the resulting mixture was separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (dichloro-methane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-e852e742bd6347e19b73345b2036ab4c
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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