Sodium Hydroxide → 7-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1521340Notes

Reaction equation

HRID 1521340 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13]CC)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 672614887-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (step 2) (30.81 g, 114 mmol) in MeOH (172 ml) was treated with 2M NaOH (172 ml, 343 mmol) and the mixture was heated to 60° C. for 40 minutes.The volatile solvent was removed in vacuo and the crude material was treated with 2M sodium bisulfate solution to adjust the pH to 6-7. The resulting solid was collected by filtrationand added to water (400 ml). The mixture was stirred and heated to 90° C. for 1 h. After cooling to RT, the suspension was filtered and dried in a vacuum over at 40° C. to afford the title product;

Workup

  1. customThe volatile solvent was removed in vacuo
  2. additionthe crude material was treated with 2M sodium bisulfate solution
  3. filtrationThe resulting solid was collected by filtrationand
  4. additionadded to water (400 ml)
  5. temperatureheated to 90° C. for 1 h
  6. temperatureAfter cooling to RT
  7. filtrationthe suspension was filtered
  8. customdried in a vacuum over at 40° C.

Sources & evidence

ORD record
ord-34e7c1e6e43845ad9ca3f5b26591d3d0
Source dataset
uspto-grants-2015_07
Patent number
US09073921B2

Reaction notes

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