Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | HCID 2734217 | — |
| Reactant | 2-[4-(trifluoromethyl)phenyl]pyrrolidine | HCID 3701153 | — |
| Reactant | N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide | HCID 11507840 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 11539545 | HCID 11539545 | 27% |
Reaction Steps
Bis(dibenzylideneacetone)palladium (3.6 mg) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (3.7 mg) were mixed in dry toluene (2 mL) under argon for 5 minutes. To this mixture were added cesium carbonate (41 mg), 2-[4-(trifluoromethyl)phenyl]pyrrolidine (15 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 20 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. Aqueous sodium bicarbonate (5 mL) was added and the mixture was extracted with ethyl acetate (3×3 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by vacuum liquid chromatography to furnish 7.6 mg (27% yield) of the title compound as an oil. LC-MS-TOF (m/z) 445 (MH+); tR=3.91, (UV, ELSD) 98%, 99%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601870B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-1b4c0f5140f74cbc8eea96a2cacdd4d0 |
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| Source note | uspto-grants-2009_10 |
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