Hydrochloric Acid → 8-Chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 717830Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([O:10]C)=[O:9])[CH:7]=1.[OH-].[Na+].O.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate (0.18 g, 0.57 mmol) in tetrahydrofuran (3 mL) was treated with 1 M sodium hydroxide in water (1.7 mL, 1.7 mmol) and stirred at 20° C. for 6 hours. The reaction mixture was concentrated, diluted with water, cooled to 0° C., and treated with 1 M hydrogen chloride in water (2.3 mL, 2.3 mmol) dropwise. The resultant suspension was filtered to give the desired product (0.17 g, quantitative) that was used without further purification. LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.0. found: 290.9.

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with water
temperaturecooled to 0° C.
filtrationThe resultant suspension was filtered

Sources & evidence

ORD record: ord-91f554a5b32149e3960b2d0f3b75430b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193721B2

Reaction notes

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