Hydrochloric Acid → 8-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 931032Notes

Reaction equation

HRID 931032 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C1COCC1.[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[C:3]2[N:4]([C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118378965Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 1183788958-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acidYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (490 mg) in a mixed solvent of THF (9 mL) and ethanol (3 mL) was added 8N aqueous sodium hydroxide solution (273 μL), and the mixture was stirred at room temperature for 1.5 hr, and then at 50° C. for 1 hr. The reaction solution was neutralized with 6N hydrochloric acid under ice-cooling, and the obtained solid was collected by filtration, and washed with water and IPE to give the title compound (380 mg).

Workup

  1. waitat 50° C. for 1 hr
  2. temperaturecooling
  3. filtrationthe obtained solid was collected by filtration
  4. washwashed with water and IPE

Sources & evidence

ORD record
ord-fdd8e0497502470e829d4544b98941c4
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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