Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5,6-Dichloro-2-trifluoromethylbenzimidazole | HCID 16859 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 3,4-Dichlorobenzeneboronic acid | HCID 2734330 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 178506264 | HCID 178506264 | — |
Reaction Steps
Compound number 258 (i.e., 6-chloro-5-(3,4-dichlorophenyl)-2-trifluoromethylbenzimidazole) was prepared as follows. A 100-mL round-bottom flask was purged and maintained with an inert atmosphere of nitrogen. 5,6-dichloro-2-(trifluoromethyl)-1H-1,3-benzodiazole (200 mg, 0.78 mmol, 1.00 equiv), 1,4-dioxane (30 mL), (3,4-dichlorophenyl)boronic acid (229 mg, 1.20 mmol, 2.00 equiv), sodium carbonate (191 mg), water (8 mL) and Pd(PPh3)4 (34.7 mg) was placed into the flask. The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 82.4 mg (29%) of 6-chloro-5-(3,4-dichlorophenyl)-2-trifluoromethylbenzimidazole as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09359305B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-817ec8c702174c919db82a8ad9292103 |
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| Source note | uspto-grants-2016_06 |
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