Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| 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 66521378 | HCID 66521378 | 31% |
Reaction Steps
Imidazole (42 mg), cesium carbonate (340 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (74 mg), and copper iodide (50 mg) were added to a tube containing a N,N-dimethylacetamide (2 ml) solution containing 5-bromopyridin-3-amine (90 mg) in a nitrogen atmosphere and the tube was sealed, followed by stirring at 150° C. for 14.5 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 10:1), and a brown solid of 5-(1H-imidazol-1-yl)pyridin-3-amine (25.8 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08895585B2 |
|---|
| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-ed4c0f448b584d5f878d8482a4ec2e7a |
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| Source note | uspto-grants-2014_11 |
|---|