Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Trifluoromethyl)phenylboronic acid | HCID 2734388 | — |
| Reactant | HCID 136359513 | HCID 136359513 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 71293463 | HCID 71293463 | 3.6% |
Reaction Steps
Intermediate 8 (900 mg, 2.77 mmol), 3-trifluoromethylphenylboronic acid (1.05 g, 5.54 mmol), Et3N (925 μL, 6.6 mmol), and copper (II) acetate (1.0 g, 5.54 mmol) were dissolved in DCE (25 mL), and the reaction mixture was stirred at 80° C. for 18 hours. After cooling to RT the reaction mixture was partitioned between DCM and water. The organic layer was separated, washed with water, followed by brine, then dried (MgSO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 3-10% MeOH in DCM and then using HPLC system 1 to yield the title compound as an orange solid (47 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09023855B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-15627c22287a4b538d78c8d686d3efe9 |
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| Source note | uspto-grants-2015_05 |
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