p-Chlorophenacyl bromide → 8-Bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine

HRID 231532

Reaction equation

HRID 231532 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.C(=O)([O-])O.[Na+]>C(O)C>[Br:8][C:7]1[C:2]2[N:3]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:1]=2)[CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 516892Sodium BicarbonateHCID 27639713-Bromo-5-chloropyridin-2-amine

Product 1

HCID 142349178-Bromo-6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17 g (82 mmol) of 2-amino-3-bromo-5-chloropyridine dissolved in 150 ml of ethanol are reacted with 29 g of 2-bromo-1-(4-chlorophenyl)-1-ethanone and 14 g of sodium hydrogen carbonate. The mixture is brought to the refluxing temperature for 6 h and cooled. The precipitate is filtered off and rinsed with CH2Cl2, and the filtrate is concentrated under reduced pressure. After recrystallization of the evaporation residue in ethyl acetate, the compound melts at 178° C.

Workup

  1. temperaturecooled
  2. filtrationThe precipitate is filtered off
  3. washrinsed with CH2Cl2
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customAfter recrystallization of the evaporation residue in ethyl acetate

Sources & evidence

ORD record
ord-8a2f27f02afd4b7b85817dfa22b20cfb
Source dataset
uspto-grants-1989_07
Patent number
US04847263

Linked notes

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