2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester → 4-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

HRID 622948Notes

Reaction equation

HRID 622948 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)C>C(O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[N:6]([CH2:5][C:4]([OH:22])=[O:3])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 143904722-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester

Product 1

HCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (7.00 g, 0.0194 mole) sodium hydroxide pellets (0.88 g, 0.0220 mole), and 95% ethanol (100 ml) was refluxed for 1 hr. The reaction mixture was cooled and filtered. The filter cake (7.3 g) was dissolved in warm water, acidified with concentrated hydrochloric acid, and chilled. The precipitated solid was collected by filtration and the filter cake was rinsed with water, giving 5.6 g (87%) of crystals. Recrystallization from tetrahydrofuran-methanol gave 5.4 g of white needles, mp 264°-267° C.

Workup

  1. temperaturewas refluxed for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. dissolutionThe filter cake (7.3 g) was dissolved in warm water
  5. temperaturechilled
  6. filtrationThe precipitated solid was collected by filtration
  7. washthe filter cake was rinsed with water

Sources & evidence

ORD record
ord-9cbd819cbb80491e915f984f2722af62
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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