HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Bromopyridine → 5-(3-Pyridinyl)-4-pentyn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Bromopyridine | HCID 12286 | — |
| Reactant | 4-Pentyn-1-ol | HCID 79346 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 5-(3-Pyridinyl)-4-pentyn-1-ol | HCID 10797061 | — |
Reaction Steps
3-Bromopyridine (5.4 g, 34.2 mmol) was dissolved in triethylamine (10 ml) and degassed under nitrogen. 4-Pentyn-1-ol (3.50 ml, 37.6 mmol) was added followed by bis(triphenylphosphine)palladium (II) chloride (0.245 g, 0.349 mmol) and copper(I)iodide (0.136 g, 0.714 mmol) and the resulting mixture was stirred and heated under reflux for 20 mins. when a dark brown sludge was obtained. The mixture was cooled to rt and partitioned between EtOAc (200 ml) and water (50 ml).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08802684B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-5f75e3fd1aa54912af11b2f0fa5ff95b |
| Source note | uspto-grants-2014_08 |