Buchwald–Hartwig amination, record ord-316cf52c137541f4a2a9960bf7cb84d3
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 | 92.54% |
Conditions
- Temperature
- 100 °C
Yield
- 93% of Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
Palladium acetate (65 mg, 0.29 mmol) and RuPhos (271mg, 0.58mmol) were dissolved in toluene (10 mL), degassed and purged with nitrogen and warmed to 50°C for 15 minutes. In a separate vessel, were mixed 3-bromo-2-methyl pyridine (1.00g, 5.81 mmol), BOC-piperazine (1.08g, 5.81mmol), sodium tertbutoxide and toluene (17 mL). The mixture was degassed, purged with nitrogen and warmed to 50°C. The catalyst was transferred to the reaction vessel and the mixture degassed and purged with nitrogen. The reaction was heated at 100°C overnight under nitrogen. The mixture was filtered through GF/F paper, washing with MeOH. The filtrate was concentrated to provide a dark brown gum. The gum was purified by flash silica chromatography, elution gradient 30 to 80% EtOAc in heptane. Pure fractions were ev
The source
This record comes from experimental reaction archive (ord-316cf52c137541f4a2a9960bf7cb84d3). Open the source and check it against what is on this page.
experimental reaction archive record ord-316cf52c137541f4a2a9960bf7cb84d3 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.