Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Amino-5-bromopyridine | HCID 817681 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 66521213 | HCID 66521213 | 68% |
Reaction Steps
Pyrazole (42 mg), cesium carbonate (340 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (74 mg), and copper iodide (50 mg) were added to a DMAc (2 ml) solution containing 5-bromopyridin-3-amine (90 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 150° C. for 15 hours. The reaction solution was adjusted to room temperature and water was added, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 10:1). A brown solid of 5-(pyrazol-1-yl)pyridin-3-amine (56.7 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09051310B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-5440768b8ca24408b051407adebe7834 |
|---|
| Source note | uspto-grants-2015_06 |
|---|