Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | 2,6-Dibromopyridine | HCID 12274 | — |
| Reactant | tert-butyl N-(prop-2-yn-1-yl)carbamate | HCID 11073648 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 54504767 | HCID 54504767 | — |
Reaction Steps
A solution of 2,6-dibromopyridine 20-1 (111 g, 468 mmol) and N-BOC-propargylamine (80.0 g, 515 mmol) in 500 ml of triethylamine at 0° C. was treated with copper(I) iodide (2.23 g, 11.7 mmol). The mixture was purged with argon and then dichlorobis(triphenylphosphine)-palladium(II) 8.22 g, 11.7 mmol) was added. The solution was stirred at 0° C. for one hour, then at room temperature for 16 hours. The solution was diluted with 250 mL ether and washed with H2O (4×100 mL). The organic extract was washed with brine and dried over Na2SO4. The solvents were removed in vacuo and the crude product was purified by silica gel chromatography (25% EtOAc/hexane) to afford 20-2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06017926 |
|---|
| Source dataset | uspto-grants-2000_01 |
|---|
| ORD ID | ord-aaa93a6aef8e459cb853c45b80b7a59d |
|---|
| Source note | uspto-grants-2000_01 |
|---|
