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

HRID 1016639Notes

Reaction equation

HRID 1016639 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=O.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1.O>CN(C)C=O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=3)[N:19]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 661742-Amino-5-chloropyridineHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 7176476-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridineYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-1-(4-chlorophenyl)ethanone (9.08 g, 39 mmol) was added to a solution of 5-chloro-2-pyridinamine (5.0 g, 39 mmol) in dimethylformamide (100 mL) and the mixture was heated under reflux for 20 h. The mixture was cooled and poured into water (400 mL) and the solid was collected. The solid was dissolved in dichloromethane (300 mL), washed with water (50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallised from ethanol/water and the solid was collected and dried in vacuo to give the title compound (0.9 g, 9%). 1H NMR (360 MHz, CDCl3) δ 8.17 (1H, d, J 2.0 Hz), 7.87 (2H, d, J 8.9 Hz), 7.81 (1H, s), 7.56 (1H, d, J 9.5 Hz), 7.41 (2H, d, J 8.9 Hz), and 7.16 (1H, dd, J 9.5, 2.0 Hz). n/z (ES+) 263, 265 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 h
  3. temperatureThe mixture was cooled
  4. customthe solid was collected
  5. dissolutionThe solid was dissolved in dichloromethane (300 mL)
  6. washwashed with water (50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was recrystallised from ethanol/water
  10. customthe solid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-742d6ba84ca64128aef8e0daccca9c2b
Source dataset
uspto-grants-2002_11
Patent number
US06476045B2

Reaction notes

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