Sodium Bicarbonate → 7-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridine

HRID 1358245Notes

Reaction equation

HRID 1358245 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13](=O)[CH2:14]Br.C([O-])(O)=O.[Na+]>C(O)C>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:14]=[C:13]([C:12]3[CH:17]=[CH:18][C:19]([CH3:20])=[C:10]([CH3:9])[CH:11]=3)[N:1]=[C:2]2[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5818662-Amino-4-chloropyridineHCID 37031132-Bromo-1-(3,4-dimethylphenyl)ethan-1-one

Product 1

HCID 98815617-Chloro-2-(3,4-dimethylphenyl)imidazo[1,2-a]pyridineYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-amino-4-chloro-pyridine (0.39 g, 3.03 mmol) in ethanol (25 ml) was added 3,4-dimethyl-phenacylbromide (0.69 g, 3.03 mmol). The reaction mixture was stirred under reflux conditions for 16 h, poured into sat. NaHCO3 solution (70 ml) and extracted with dichloromethane (70 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give the crude product as a brown solid (0.84 g). Further purification by column chromatography on silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane yielded the title compound (0.54 g, 69%) as a pale yellow solid, m.p. 144° C. and MS: m/e=256.2 (M+).

Workup

  1. extractionextracted with dichloromethane (70 ml)
  2. washThe combined organic layers were washed with brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give the crude product as a brown solid (0.84 g)
  6. customFurther purification by column chromatography
  7. customon silica gel (ethyl acetate/toluene 1:9) and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d1025be599ce42369019ca833e945681
Source dataset
uspto-grants-2003_07
Patent number
US06596731B2

Reaction notes

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