Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 3-Iodo-2-propoxypyridine | HCID 42553132 | — |
| Reactant | 2-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine | HCID 87550402 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 25181650 | HCID 25181650 | 10% |
Reaction Steps
Into a flamed flask flushed with nitrogen a mixture of CuI (19.4 mg. 0.1 mmol)), K3PO4 (425 mg, 2 mmol), ethylene glycol (112 μL), 3-iodo-2-propoxypyridine (263 mg, 1 mmol) in 1 mL of n-Butanol were added 255 mg of the compound of Example 3 dissolved in 1 mL of n-Butanol. The suspension was heated at 100° C. for 5 h. The reaction mixture was then cooled to r.t., diluted with EtOAc, washed with aq., NaHCO3 and water, dried over Na2SO4 and evaporated to dryness in vacuo. After the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 8:2. affording the title product (32 mg, 10%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08518916B2 |
|---|
| Source dataset | uspto-grants-2013_08 |
|---|
| ORD ID | ord-9487ee5ee34645b489a8be11a9b2cc21 |
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| Source note | uspto-grants-2013_08 |
|---|
