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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203014Generated: October 31, 2026

Toluene → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((5-(difluoromethyl)-3-thienyl)methoxy)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203014

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant3-Thiophenemethanol, 5-(difluoromethyl)-HCID 89690330—
Reactant4-Bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinoneHCID 121386204—
SolventWaterHCID 962—
Product1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-((5-(difluoromethyl)-3-thienyl)methoxy)pyridin-2(1H)-oneHCID 8969028251.6%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4-bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (100 mg), (5-(difluoromethyl)-3-thienyl)methanol (88 mg), potassium tert-butoxide (109 mg) and toluene (3 ml) was heated at 100° C. for 1 h. The reaction mixture was then cooled to room temperature, poured into water and extracted with EtOAc-THF. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from IPA-IPE to give the title compound (64.1 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-af5d5c94ad754756aa1c7a0c6fb3182c
Source noteuspto-grants-2016_06