Ethanol → 7-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 79421Notes

Reaction equation

HRID 79421 reaction equation
[F: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.O1CCCC1.C(O)C.O.[OH-].[Li+]>O>[F: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

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67259301Ethyl 7-fluoroimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 672607377-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acidYield 78.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 7-fluoroimidazo[1,2-a]pyridine-3-carboxylate (8.0 g; 44.4 mmol) was mixed with tetrahydrofuran (225 mL), ethanol (110 mL) and water (55 mL). Lithium hydroxide monohydrate (0.962 g; 22.9 mmol) was added. The mixture was stirred at ambient temperature for 16 hours. The mixture was concentrated under reduced pressure to remove tetrahydrofuran and ethanol. 2 N hydrochloric acid was added to the mixture to adjust to pH 3. A white precipitate formed which was collected by filtration and dried under high vacuum to give 7-fluoroimidazo[1,2-a]pyridine-3-carboxylic acid as a white solid (6.3 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove tetrahydrofuran and ethanol
  3. addition2 N hydrochloric acid was added to the mixture
  4. customA white precipitate formed which
  5. filtrationwas collected by filtration
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-43ca03de019b45c29cd0291d65ebb94b
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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