Buchwald–Hartwig amination, record ord-4147e405915e4ea7b4607546c536b535
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromo-2-methylpyridine | C₆H₆BrN | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate | C₁₅H₂₃N₃O₂ | 82.86% |
Conditions
- Temperature
- 100 °C
Yield
- 83% of Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
RuPhos (0.543 g, 1.16 mmol) and palladium (II) acetate (0.131 g, 0.58 mmol) were suspended in toluene (15 mL) at ambient temperature. The resulting mixture was degassed and purged several times and warmed to 50°C under nitrogen for 20 mins. In a separate vessel were mixed 3-bromo-2-methylpyridine (2 g, 11.63 mmol), tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate (2.67 g, 83 %), sodium tertbutoxide (1.676 g, 17.44 mmol) and toluene. The mixture was degassed and purged with nitrogen several times and warmed to 50°C. The catalyst solution was added to the reaction vessel and the resulting mixture degassed and purged wtih nitrogen. The reaction was heated at 100°C overnight. The reaction mixture was allowed to cool to ambient temperature and filtered through GF/F paper, washing
The source
This record comes from experimental reaction archive (ord-4147e405915e4ea7b4607546c536b535). Open the source and check it against what is on this page.
experimental reaction archive record ord-4147e405915e4ea7b4607546c536b535 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.