N-bromobutanimide → 4-(3-Bromo-2-methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 1851188Notes

Reaction equation

HRID 1851188 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:9]=[C:8]([C:10]3[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=3)[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:6][N:5]2[CH:24]=1.[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:25][C:24]1[N:5]2[CH:6]=[C:7]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:8]([C:10]3[CH:11]=[CH:12][C:13]([CH:14]=[O:15])=[CH:16][CH:17]=3)=[N:9][C:4]2=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 867030344-(2-Methyl-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 867030354-(3-Bromo-2-methyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.2 g (0.64 mmol) 4-(2-Methyl-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)benzaldehyde, described in intermediate example 15.1, are dissolved in 2.8 mL chloroform and treated with 170 mg (0.96 mmol) N-bromosuccinimide. The mixture is heated for 2.5 hours at reflux. The solvent is removed and the residue purified by chromatography (silicagel, dichloromethane/methanol). 198.4 mg (75.3%) of the desired compound are obtained.

Workup

  1. temperatureThe mixture is heated for 2.5 hours
  2. temperatureat reflux
  3. customThe solvent is removed
  4. customthe residue purified by chromatography (silicagel, dichloromethane/methanol)

Sources & evidence

ORD record
ord-e726bf5da18744edb816c37e5bfd569a
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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