Water → 6-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 706733Notes

Reaction equation

HRID 706733 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([O:13]CC)=[O:12])=[CH:9][N:10]=2)[CH:7]=1.O.[OH-].[Li+].O.C1COCC1>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67976050Ethyl 6-fluoroimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 552681956-Fluoroimidazo[1,2-a]pyridine-3-carboxylic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 6-fluoroimidazo[1,2-a]pyridine-3-carboxylate (0.10 g, 0.48 mmol) and lithium hydroxide monohydrate (0.020 g, 0.48 mmol) were added to a mixture of water, THF and ethanol (1:2:1) and heated in a sealed vial at 65° C. for 6 hours. The solvent was removed by rotary evaporation to yield 87 mg of the desired product. MS (ES+APCI) m/z=181.1 (M+H).

Workup

  1. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-d9a8e9c6dd164383b77d8541e4a5cd4e
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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