Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1H-1,2,3-Triazole | HCID 67516 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Reactant | 3-Bromo-4-methylpicolinonitrile | HCID 21952574 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90412434 | HCID 90412434 | 40.3% |
Reaction Steps
In a microwave vial was dissolved 2H-1,2,3-triazole (0.22 mL, 3.8 mmol) and CuI (26 mg) in DMF (4 mL). The reaction mixture was degassed with N2 and 3-bromo-4-methylpicolonitrile (300 mg, 1.5 mmol) was added followed by trans-N,N′-dimethyl-1,2-cyclohexanediamine (41 μL, 0.3 mmol) and Cs2CO3 (844 mg, 2.6 mmol). The reaction mixture was heated at 120° C. for 1 h in a microwave reactor. Then H2O was added and the mixture extracted with EtOAc. The combined organic layers were dried (MgSO4). Purification via silica gel chromatography (0-50% EtOAc in heptane) gave the title compound (112 mg, 27%). MS (ESI) mass calcd. for C9H7N5, 185.2; m/z found 186 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062078B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-ad90c9539bfc4478addd5e143b8df951 |
|---|
| Source note | uspto-grants-2015_06 |
|---|
