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

HRID 1844136Notes

Reaction equation

HRID 1844136 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 23A; 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 mixture was concentrated under reduced pressure and the residue was acidified with 1N hydrochloric acid. The solid was triturated, 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 mixture was concentrated under reduced pressure
  3. customThe solid was triturated
  4. filtrationfiltered off
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d401ba0733eb47578e3a19b1b1d2f014
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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