Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Bromopyridine-2-carbonitrile | HCID 817154 | — |
| Reactant | 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride | HCID 2734913 | — |
| Reactant | 2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine | HCID 87550402 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 25181924 | HCID 25181924 | 10.3% |
Reaction Steps
A mixture of the compound of Example 3 (0.102 g, 0.48 mmol), 5-bromo-2-cyanopyridine (0.073 g, 0.40 mmol), cesium carbonate (0.658 g, 2 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (8.8 mg, 0.05 mmol), palladium(II)acetate (0.0046 mg, 0.05 mmol), in anhydrous and degassed THF (3 mL) was heated in a microwave oven at 110° C. for 15 min in a sealed vessel. The reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 1:1) affording the title product (0.013 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08518916B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-f10bc29da49e4dea94837f08aaa928d6 |
|---|
| Source note | uspto-grants-2013_08 |
|---|