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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202895Generated: October 31, 2026

Tributylphosphine → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-methyl-2-thienyl)methoxy)pyridin-2(1H)-one

https://huagongshe.com/reaction/2202895

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylphosphineHCID 13831—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
Reactant(4-Methylthiophen-2-yl)methanolHCID 2795527—
Reactant1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-oneHCID 89691084—
SolventTetrahydrofuranHCID 8028—
Product1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-methyl-2-thienyl)methoxy)pyridin-2(1H)-oneHCID 8970221720.6%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (4-methyl-2-thienyl)methanol (138 mg) and tributylphosphine (322 mg) in THF (10 ml) was added 1,1′-(azodicarbonyl)dipiperidine (401 mg) in dry THF (5 ml). The mixture was stirred under sonication at 60° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was diluted with DCM, 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 (43 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-b27b5037c0b548a6b54543b11b39463e
Source noteuspto-grants-2016_06