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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202953Generated: October 31, 2026

Tributylphosphine → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((3-fluorobenzyl)oxy)pyridin-2(1H)-one

https://huagongshe.com/reaction/2202953

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylphosphineHCID 13831—
Reactant3-Fluorobenzylic alcoholHCID 68008—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
Reactant1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-oneHCID 89690281—
SolventTetrahydrofuranHCID 8028—
Product1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((3-fluorobenzyl)oxy)pyridin-2(1H)-oneHCID 8970240021.7%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (3-fluorophenyl)-methanol (134 mg) and tributylphosphine (322 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (401 mg). The mixture was stirred under sonication at 60° C. for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with DCM (100 ml), and the DCM layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (45 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-384689d7c9e7490b994636fbf0e5a378
Source noteuspto-grants-2016_06