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

HRID 706618Notes

Reaction equation

HRID 706618 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 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 overnight. The mixture concentrated under reduced pressure to remove tetrahydrofuran and ethanol. Hydrochloric acid (2N) was added to aqueous mixture to adjust to pH 3. White precipitate formed and was filtered off with drying under high vacuum overnight to give 7-fluoroimidazo[1,2-a]pyridine-3-carboxylic acid as a white solid (6.3 g).

Workup

  1. concentrationThe mixture concentrated under reduced pressure
  2. customto remove tetrahydrofuran and ethanol
  3. additionHydrochloric acid (2N) was added to aqueous mixture
  4. customWhite precipitate
  5. customformed
  6. filtrationwas filtered off
  7. customwith drying under high vacuum overnight

Sources & evidence

ORD record
ord-fb270e9640ee40cd8b25ad7c04376fb6
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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