Potassium Carbonate → 1-(4-ethylbenzyl)-5-bromopyridin-2(1H)-one

HRID 549985Notes

Reaction equation

HRID 549985 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:9]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5995285-Bromo-2-hydroxypyridineHCID 122315601-(Bromomethyl)-4-ethylbenzene

Product 1

HCID 582425001-(4-ethylbenzyl)-5-bromopyridin-2(1H)-oneYield 90.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-1H-pyridin-2-one (1.04 g) and 4-ethylbenzyl bromide (1.43 g) were dissolved in N,N-dimethylformamide (15 ml), and thereto was added potassium carbonate (1.66 g). The mixture was stirred at room temperature overnight, diluted with ethyl acetate, and washed successively with water and brine. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-3:1) to give 5-bromo-1-(4-ethylphenylmethyl)-1H-pyridin-2-one (1.58 g) as colorless crystals. APCI-Mass m/Z 292/294 (M+H).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-3:1)

Sources & evidence

ORD record
ord-e38160ba2f6f4b019622e7c0c0c20a85
Source dataset
uspto-grants-2011_05
Patent number
US07943788B2

Reaction notes

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