Tetrahydrofuran → 8-[(2-Fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 64401Notes

Reaction equation

HRID 64401 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([O:18]CC)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.C1COCC1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 53732806Ethyl 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 204590498-[(2-Fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.16 g of ethyl 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate were added 20 ml of THF, 40 ml of ethanol, and 20 ml of a 1 M aqueous sodium hydroxide solution, followed by stirring for 4 days. The solvent was evaporated under reduced pressure, and water and 1 M hydrochloric acid were added thereto. The insoluble material was collected by filtration and dried to obtain 1.99 g of 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and 1 M hydrochloric acid
  2. additionwere added
  3. filtrationThe insoluble material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e19b7df0a6d7480c9d81daf94cae7218
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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