Methyl iodide → 5-(5-Bromo-3-pyridinyl)-1-methyl-2-pyrrolidinone

HRID 712755

Reaction equation

HRID 712755 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:16]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:12][C:11](=[O:13])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:12]([CH3:16])[C:11](=[O:13])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1176674955-(5-Bromopyridin-3-YL)pyrrolidin-2-one

Product 2

HCID 196943295-(5-Bromo-3-pyridinyl)-1-methyl-2-pyrrolidinoneYield 146.5%HCID 1176674955-(5-Bromopyridin-3-YL)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(5-Bromo-pyridin-3-yl)-pyrrolidin-2-one is prepared as described in Example 76. To a solution of 5-(5-bromo-pyridin-3-yl)-pyrrolidin-2-one (202 mg, 0.84 mmol) in THF (5.0 mL) is added 60% NaH (50 mg, 1.3 mmol). The mixture is stirred at room temperature for 5 min and methyl iodide (0.078 mL, 1.3 mmol) is then added dropwise. The mixture is stirred at room temperature for 16 h. The mixture is then concentrated and purified by normal phase chromatography to give 157 mg of 5-(5-bromo-pyridin-3-yl)-1-methyl-pyrrolidin-2-one.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 h
  2. concentrationThe mixture is then concentrated
  3. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-0bcae626d45344c9a3cfcdf736f5404d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Linked notes

Loading…