N-Bromosuccinamide → 3-(benzyloxy)-5-bromo-1-(4-butylphenyl)pyridin-4(1H)-one

HRID 571047Notes

Reaction equation

HRID 571047 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:26]NC(=O)CCC(N)=O>CC(O)=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([Br:26])=[CH:12][N:11]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH3:25])=[CH:20][CH:21]=2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 674195993-(benzyloxy)-1-(4-butylphenyl)pyridin-4(1H)-one

Product 1

HCID 674190343-(benzyloxy)-5-bromo-1-(4-butylphenyl)pyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(benzyloxy)-1-(4-butylphenyl)pyridin-4(1H)-one (705 mg, 2.1 mmol) in AcOH (21 mL) was added N-bromosuccinamide (414 mg, 2.3 mmol) and the reaction mixture was stirred at room temperature. After 1 h, the mixture was concentrated under reduced pressure and purified by flash chromatography (50 g SiO2, 0-70% ethyl acetate/hexanes) to provide 3-(benzyloxy)-5-bromo-1-(4-butylphenyl)pyridin-4(1H)-one. LC/MS (M+H)+ 412/414.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography (50 g SiO2, 0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bdc6f27d6a104e5d92a7e98d0c899522
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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