Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-(Dicyclohexylphosphino)biphenyl | HCID 2734216 | — |
| Reactant | Methyl 2-bromo-4-(trifluoromethyl)benzoate | HCID 46311084 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59438405 | HCID 59438405 | 30.4% |
Reaction Steps
To 30 mg (0.0318 mmol) Pd2 dba3, 37.9 mg (0.106 mmol) 2-(dicyclohexyl-phosphino)biphenyl and 315 mg (1.484 mmol) potassium phosphate tribasic under argon at room temperature, was added a solution of 105.2 ul (1.272 mmol) pyrrolidine in 5.5 ml toluene dry, followed by 300 mg (1.06 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester (CAS: 328-89-2). The reaction mixture was heated at 80° C. overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The suspension was filtered. The filtrate was concentrated in vacuo. The residue was purified on silica (Eluent: heptane/ethyl acetate 0 to 10%) to provide 88 mg (30.4%) of the title compound as an orange oil. MS (m/e): 274.3 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09067911B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-16cc00e23cd04fc2989771c569c9664d |
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| Source note | uspto-grants-2015_06 |
|---|