Hydrochloric Acid → 8-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 923504Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[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.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[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

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5.41 g of ethyl 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate in 32 ml of ethanol was added dropwise 6.2 ml of a 5 M aqueous sodium hydroxide solution, followed by stirring at 60° C. for 1.5 hours. To the reaction mixture was added dropwise 15.8 ml of 2 M hydrochloric acid at 50° C., and then 1.5 ml of a 2 M hydrochloric acid was added thereto. The insoluble materials were collected by filtration and the solid was washed with ethanol/water=1:1 to obtain 3.46 g of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid.

Workup

filtrationThe insoluble materials were collected by filtration
washthe solid was washed with ethanol/water=1:1

Sources & evidence

ORD record: ord-ba970a72d27d4078810683d8b6ff2cb7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278968B2

Reaction notes

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