Buchwald–Hartwig amination, record ord-218b24f2d22444388b751f136d342319
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-Bromopyridine | C₅H₄BrN | |
| Reactant | (1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane | C₁₀H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (1S,4S)-5-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate | C₁₅H₂₁N₃O₂ | 98.65% |
Conditions
- Temperature
- 85 °C
Yield
- 99% of tert-butyl (1S,4S)-5-(3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate.
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.055 g, 0.06 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.075 g, 0.12 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (29.7 ml) was added and the resulting mixture heated to 90°C for 10 minutes then cooled to room temperature. In a second reaction vessel was mixed sodium tert-butoxide (0.465 g, 4.84 mmol), 3-bromopyridine (0.321 ml, 3.33 mmol) and (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.601 g, 3.03 mmol) and toluene (29.7 ml). The mixture was evacuated and purged with nitrogen 3 times. The solution of catalyst was added to the reaction mixture and the resulting mixture was heated at 85 °C for 64 hours. The reaction mixture was cooled to RT and filtered through celite a
The source
This record comes from experimental reaction archive (ord-218b24f2d22444388b751f136d342319). Open the source and check it against what is on this page.
experimental reaction archive record ord-218b24f2d22444388b751f136d342319 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.