Ethyl Acetate → HCID 23090850, compound

HRID 1820008Notes

Reaction equation

HRID 1820008 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][N:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 64246602-Bromo-5-bromomethylpyridine

Product 1

HCID 23090850HCID 23090850, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-bromo-5-(bromomethyl)pyridine (9.06 g, 36.1 mmol), pyrrolidine (3.62 ml, 43.3 mmol) and potassium carbonate (9.98 g, 72.2 mmol) in acetonitrile (45 ml) was stirred at room temperature for 6 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous potassium carbonate solution and saturated, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate) to give the title compound (7.31 g).

Workup

  1. washthe mixture was washed with saturated aqueous potassium carbonate solution
  2. dry with materialsaturated, and dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-87e4165647f14dc0be452b773cbb80e7
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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