Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 86598713 | HCID 86598713 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 68444255 | HCID 68444255 | — |
Reaction Steps
A mixture of 2-[6-bromo-3-pyridazinyl]-(1S,4S)-5-tert-butoxycarbonyl-2,5-diazabicyclo-[2.2.1]-heptane (2.0 g; 5.6 mmol), phenylacetylene (2.4 ml; 22.6 mmol), palladacycle (105 mg; 0.11 mmol), CuI (106 mg; 0.56 mmol), diisopropylethylamine (0.97 ml; 5.6 mmol) and dioxane (20 ml) was stirred at 100° C. for 40 hours. Aqueous sodium hydroxide (50 ml; 1 M) was added. The mixture was extracted with dichloromethane (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 1.0 g (48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07750011B2 |
|---|
| Source dataset | uspto-grants-2010_07 |
|---|
| ORD ID | ord-f6a9fba2f7dc4711a9023cdad72f3859 |
|---|
| Source note | uspto-grants-2010_07 |
|---|
