Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(Trifluoromethyl)pyrazole | HCID 1807034 | — |
| Reactant | 1-(4-Bromophenyl)Cyclopropanecarbonitrile | HCID 2795273 | — |
| Reactant | (1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine | HCID 13822957 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66661552 | HCID 66661552 | — |
Reaction Steps
To a solution of 1-(4-bromophenyl)cyclopropanecarbonitrile (600 mg, 0.003 mol), 3-(trifluoromethyl)-1H-pyrazole (441 mg, 0.00324 mol) in toluene (2 mL, 0.02 mol) and N,N-dimethylformamide (3 mL, 0.04 mol) were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (77 mg, 0.00054 mol), copper(I) iodide (51 mg, 0.00027 mol), and potassium carbonate (784 mg, 0.00567 mol). The mixture was microwave irradiated at 200° C. for 60 minutes and then filtered. The filtrate was diluted with methanol, and the product from the filtrate was isolated and purified using prep-HPLC. Additional product could be obtained from the precipitate by dissolving the precipitate in EtOAc, washing with satd. NaHCO3, brine, drying with MgSO4, and concentrating for purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07776874B2 |
|---|
| Source dataset | uspto-grants-2010_08 |
|---|
| ORD ID | ord-f9d80e0305e64e79b934ed2113d77b3a |
|---|
| Source note | uspto-grants-2010_08 |
|---|
