Buchwald–Hartwig amination, record ord-498c0c75d66a47609408cbfbddaef8e5
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 | 5-Bromo-2-fluorotoluene | C₇H₆BrF | |
| Reactant | Methyl isonipecotate | C₇H₁₃NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate | C₁₄H₁₈FNO₂ | 0% |
Conditions
- Temperature
- 110 °C
Yield
- 0% of Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate.
Procedure
Copied from the source record, unedited
In a 100 mL round-bottomed flask methyl piperidine-4-carboxylate (2.2 g, 15.36 mmol),4-bromo-1-fluoro-2-methylbenzene (1.954 mL, 15.36 mmol),Pd2(dba)3 (0.521 g, 0.57 mmol),BINAP (0.574 g, 0.92 mmol) and sodium tert-butoxide (4.43 g, 46.09 mmol) was taken in toluene (10 mL) under N2.The resulting reaction was stirred at 110 °C for 3 hrs. LCMS did not show product MS.Material was discrded.
The source
This record comes from experimental reaction archive (ord-498c0c75d66a47609408cbfbddaef8e5). Open the source and check it against what is on this page.
experimental reaction archive record ord-498c0c75d66a47609408cbfbddaef8e5 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.