Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Pyridine N-Oxide | HCID 12753 | — |
| Reactant | HCID 66691674 | HCID 66691674 | — |
| Reactant | HCID 68386921 | HCID 68386921 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68386507 | HCID 68386507 | 22.8% |
Reaction Steps
To a solution of 751 mg [4-(cyclopropylcarbamoyl)-3-methylphenyl]boronic acid in 68.6 mL dichloromethane were added 528 mg (1.71 mmol) 6-bromo-N-(3,3,3-trifluoropropyl)-1H-benzimidazol-4-amine which was prepared according to intermediate example 1b, 623 mg copper(II)diacetate, 179 mg pyridine 1-oxide and 416 μL pyridine. The mixture was stirred at 23° C. for two days. Water was added and the mixture was extracted with dichloromethane and methanol. The organic layer was washed with water and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 188 mg (22%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09388140B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-2394e83d8cbb448ea14f202cf1470b2d |
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| Source note | uspto-grants-2016_07 |
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