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

HRID 1684906Notes

Reaction equation

HRID 1684906 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=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+].O>C(O)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68303p-Chlorophenacyl bromideHCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 8282916-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridineYield 69.9%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

2.33 g of 5-bromopyridin-2-ylamine and 3.14 g of 2-bromo-1-(4-chlorophenyl)-ethanone are placed in 110 ml of n-propanol in a round-bottomed flask. 1.58 g of sodium hydrogencarbonate are added. The mixture is heated at 80° C. for 16 h and allowed to cool to ambient temperature. 400 ml of water are added. The precipitate is collected by filtration, washed with water and dried in an oven under reduced pressure. 2.89 g of compound are obtained. 1H NMR spectrum (d6-DMSO, δ in ppm): 7.4 (d, 1H); 7.5 (d, 2H); 7.6 (d, 1H); 8.0 (d, 2H); 8.4 (s, 1H); 8.9 (s, 1H). M+H=308.

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-118f683f74dc4f439f57a274a5474846
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

Loading…