Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | 3,5-Dibromoaniline | HCID 221512 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 57813693 | HCID 57813693 | 42% |
Reaction Steps
To a solution of 3,5-dibromoaniline (0.50 g, 1.99 mmol) in DMSO (2.0 mL) was added sequentially L-Proline (0.041 g, 0.36 mmol), Cs2CO3 (1.16 g, 3.58 mmol), CuI (0.038 g, 0.20 mmol) and pyrazole (0.12 g, 1.80 mmol). The reaction mixture was degassed for 10 min and then heated to 110° C. for 48 h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled to room temperature, added water and extracted with ethyl acetate (×3). The combined organics was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 15% EtOAc-Hexane) to get the desired compound (0.18 g, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08481544B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-38c08bc298924a1aac793e2baef5b665 |
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| Source note | uspto-grants-2013_07 |
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