4-(Bromoacetyl)phenyl benzoate → HCID 67337553, compound

HRID 910639Notes

Reaction equation

HRID 910639 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17]Br)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>C(O)C>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][N:22]3[CH:17]=2)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2203054-(Bromoacetyl)phenyl benzoateHCID 516892Sodium BicarbonateHCID 113209342-Amino-5-methoxypyridine

Product 1

HCID 67337553HCID 67337553, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.33 g (corresponding to 43.68 mmol) of 4′-benzoyloxy-2-bromoacetophenone and 5.67 g (corresponding to 45.67 mmol) of 2-amino-5-methoxypyridine were dissolved in 481 mL of ethanol. The resulting solution was refluxed for 2 hours. After the reaction solution was cooled, 6.64 g (corresponding to 79.09 mmol) of sodium hydrogencarbonate was added thereto. The resulting reaction mixture was further refluxed for 4 hours. After the completion of the reaction, the solvent was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and then washed with water. After the chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/ethyl acetate=20/1), to obtain 10.20 g (corresponding to 30.87 mmol) of 2-(4′-benzoyloxyphenyl)-6-methoxyimidazo[1,2-a]pyridine (FIG. 5, Step 5).

Workup

  1. temperatureThe resulting solution was refluxed for 2 hours
  2. temperatureAfter the reaction solution was cooled
  3. customThe resulting reaction mixture
  4. temperaturewas further refluxed for 4 hours
  5. customAfter the completion of the reaction
  6. concentrationthe solvent was concentrated under reduced pressure
  7. dissolutionThe resulting residue was dissolved in chloroform
  8. washwashed with water
  9. dry with materialAfter the chloroform layer was dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-7bd3b2346b6647b2b6f31948549d0faa
Source dataset
uspto-grants-2011_09
Patent number
US08022207B2

Reaction notes

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