Lithium Hydroxide → 8-[(2,6-Difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 2401640Notes

Reaction equation

HRID 2401640 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17]([O:19]CC)=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[C:10]([CH3:12])[CH:11]=1.[OH-].[Li+]>C1COCC1.CO>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17]([OH:19])=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[C:10]([CH3:12])[CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86717882Ethyl 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 867178848-[(2,6-Difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

220 mg of ethyl 8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate (Example 20A; 0.524 mmol, 1 equivalent) were dissolved in 7 ml of THF/methanol 1:1, 2.6 ml of 1 N aqueous lithium hydroxide solution (2.6 mmol, 5 equivalents) were added and the mixture was stirred at RT for 16 h. The reaction mixture was concentrated and the residue was acidified with 1N aqueous hydrochloric acid. The solid obtained was stirred, filtered off, washed with water and dried under reduced pressure. This gave 120 mg of the title compound (60% of theory).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. customThe solid obtained
  4. stirringwas stirred
  5. filtrationfiltered off
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-bff45d08e6c34332998eb0d15f463d4e
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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