Hydrochloric Acid → 8-[(3-Fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid hydrochloride

HRID 1844184Notes

Reaction equation

[F:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[C:11]3[N:12]([C:16]([C:20]([O:22]CC)=[O:21])=[C:17]([CH3:19])[N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].[ClH:27]>C1COCC1.CO>[ClH:27].[F:1][C:2]1[C:3]([CH2:8][O:9][C:10]2[C:11]3[N:12]([C:16]([C:20]([OH:22])=[O:21])=[C:17]([CH3:19])[N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4.66 g of ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 116A, 14.2 mmol) were dissolved in 304 ml of THF/MeOH (5/1), 70.8 ml of 1 N aqueous lithium hydroxide solution (70.8 mmol) were added and the mixture was stirred at 40° C. overnight. The reaction mixture was acidified (pH about 3-4) using 1 N aqueous hydrochloric acid, and the solution was concentrated. The precipitate formed was cooled with ice-water and then filtered off with suction and dried under reduced pressure. This gave 3.97 g of the product (83% of theory).

Workup

concentrationthe solution was concentrated
customThe precipitate formed
filtrationfiltered off with suction
customdried under reduced pressure

Sources & evidence

ORD record: ord-6aeb5ea25fe74a75bd7d118872add423
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946215B2

Reaction notes

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