Water → 7-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 79438Notes

Reaction equation

HRID 79438 reaction equation
[CH3:1][C:2]1([CH3:23])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([O:20]CC)=[O:19])=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1.O.[OH-].[Li+].O1CCCC1.C(O)C.O.O>ClCCl>[CH3:1][C:2]1([CH3:23])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]([OH:20])=[O:19])=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 18504229Ethanol tetrahydrofuran waterHCID 67259610Ethyl 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 672601837-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylate (1.8 g, 5.63 mmol) and lithium hydroxide monohydrate (0.284 g, 6.75 mmol) were combined in a 250 mL round bottom flask containing tetrahydrofuran/ethanol/water (1:2:1, 56 mL). After stirring overnight at ambient temperature, the solvent was removed under vacuum to give a yellow gum. Water (20 mL) and dichloromethane was added. The aqueous layer was separated and cooled in an ice-water bath before adjusting to pH 4 with 20% citric acid. A precipitate formed and was collected by filtration. The solids were washed with a small amount of water (5 mL) and dried under vacuum to give 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid as a white solid (1.3 g).

Workup

  1. customthe solvent was removed under vacuum
  2. customto give a yellow gum
  3. customThe aqueous layer was separated
  4. temperaturecooled in an ice-water bath
  5. customA precipitate formed
  6. filtrationwas collected by filtration
  7. washThe solids were washed with a small amount of water (5 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8838e4fdff42490bb914e48ea95d024c
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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