Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromo-4-methylpyridine | HCID 817630 | — |
| Reactant | 2-(Dicyclohexylphosphino)biphenyl | HCID 2734216 | — |
| Reactant | 2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine | HCID 87550402 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 87550603 | HCID 87550603 | 6.6% |
Reaction Steps
A mixture of the compound of Example 3 (0.102 g, 0.48 mmol), 3-bromo-4-methylpyridine (0.046 g, 0.40 mmol), cesium carbonate (0.658 g, 2 mmol), 2-(dicyclohexylphosphino)biphenyl (8.8 mg, 0.024 mmol), palladium(II)acetate (0.0027 mg, 0.012 mmol), in anhydrous and degassed toluene (3 mL) was heated in a microwave oven at at 150° 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 (CHCl3-1.4 N MeOH NH3 100:0.25) affording the title product (0.008 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08518916B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-a33a5ce789494f87bb75745aea6186af |
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| Source note | uspto-grants-2013_08 |
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