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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203024Generated: November 2, 2026

Triphenylphosphine → 4-((4-Bromo-1,3-thiazol-2-yl)methoxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203024

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactant(4-Bromo-1,3-thiazol-2-yl)methanolHCID 11041630—
Reactant2-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 53384415—
Reactant1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-oneHCID 89690281—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product4-((4-Bromo-1,3-thiazol-2-yl)methoxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-oneHCID 12138623846.6%

Reaction Steps

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (4-bromo-1,3-thiazol-2-yl)methanol (69 mg) and triphenylphosphine (140 mg) in THF (6 ml) was added bis(2-methoxyethyl) azodicarboxylate (125 mg), and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH-hexane to give the title compound (37.9 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-ae9d0956ac4548dabae26ad9de339ea1
Source noteuspto-grants-2016_06