Buchwald–Hartwig amination, record ord-3870c5bc1f6548e38bd05a0e29b91f59
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 | 4-Bromo-2-methoxypyridine | C₆H₆BrNO | |
| Reactant | 3-Aminoazetidine, 3-BOC protected | C₈H₁₆N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamate | C₁₄H₂₁N₃O₃ | 100.28% |
Conditions
- Temperature
- 70 °C
Yield
- 100% of tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamate.
Procedure
Copied from the source record, unedited
A mixture of all the reactants in toluene was heated in a sealed vial at 70 °C overnight. According to LC-MS the reaction was completed and the product had been formed. Toluene was removed, water was added and the product was extracted with DCM. The organic phase was dried through phase separator and concentrated. The crude was used without further purification in the next step, EN01762-02.
The source
This record comes from experimental reaction archive (ord-3870c5bc1f6548e38bd05a0e29b91f59). Open the source and check it against what is on this page.
experimental reaction archive record ord-3870c5bc1f6548e38bd05a0e29b91f59 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.