1-Propanol → 6-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine

HRID 1891243Notes

Reaction equation

HRID 1891243 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=O.C(=O)([O-])O.[Na+].C(O)CC>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:1]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 68303p-Chlorophenacyl bromideHCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 8282916-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridineYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2.5 g (14.45 mmol) of 2-amino-5-bromopyridine, 3.37 g (14.45 mmol) of 2-bromo-4′-chloroacetophenone, 1.82 g (21.67 mmol) of sodium hydrogen carbonate and 110 ml of 1-propanol are introduced into a 250 ml three-necked flask, equipped with a magnetic stirrer and maintained under a nitrogen atmosphere. After stirring for 18 hours at 80° C., the reaction mixture is brought back to ambient temperature and diluted with 400 ml of water. The precipitate formed is recovered by filtration, washed with water, and then dried at 80° C. under reduced pressure. 3.96 g of expected product are thus isolated in the form of a beige powder.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. customis brought back to ambient temperature
  4. customThe precipitate formed
  5. filtrationis recovered by filtration
  6. washwashed with water
  7. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-1d63d015e518477e95da8f13569b58ef
Source dataset
uspto-grants-2013_08
Patent number
US08507520B2

Reaction notes

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