HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203079Generated: October 31, 2026
Tetrahydrofuran → 4-((1RS,2RS)-2-(4-chlorophenyl)-3-(trimethylsilyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
https://huagongshe.com/reaction/2203079
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 89690863 | — |
| Reactant | ((2RS,3SR)-2-(4-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)(trimethyl)silane | HCID 131735783 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-((1RS,2RS)-2-(4-chlorophenyl)-3-(trimethylsilyl)cyclopropyl)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 131735784 | 17% |
Reaction Steps
A mixture of 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (108 mg), ((2RS,3SR)-2-(4-chlorophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)(trimethyl)silane (110 mg), potassium carbonate (130 mg), PdCl2(dppf) (11.5 mg), THF (6 ml) and water (2.0 ml) was heated at 70° C. overnight. The mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (26.0 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365540B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-b019c31b49354d59b69fa50fbd29b8cb |
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| Source note | uspto-grants-2016_06 |
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