N-Bromosuccinamide → 3-(benzyloxy)-1-(biphenyl-3-yl)-5-bromopyridin-4(1H)-one

HRID 571050Notes

Reaction equation

HRID 571050 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[CH:20][CH:21]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28]NC(=O)CCC(N)=O>CC(O)=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([Br:28])=[CH:12][N:11]([C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:19]=[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 674181433-(benzyloxy)-1-(biphenyl-3-yl)pyridin-4(1H)-one

Product 1

HCID 674201973-(benzyloxy)-1-(biphenyl-3-yl)-5-bromopyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(benzyloxy)-1-(biphenyl-3-yl)pyridin-4(1H)-one (2.41 g, 6.8 mmol) in AcOH (68 mL) was added N-bromosuccinamide (2.67 g, 15 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 (80 g SiO2, 0-100% ethyl acetate/hexanes) to provide 3-(benzyloxy)-1-(biphenyl-3-yl)-5-bromopyridin-4(1H)-one. LC/MS (M+H)+ 432/434.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. custompurified by flash chromatography (80 g SiO2, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fb7072b6dfc2433f8f16a82eba73b744
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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