Buchwald–Hartwig amination, record ord-c91f5415f0604adda8f4b73dd97ab0f8
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-Bromoanisole | C₇H₇BrO | |
| Reactant | 4-Piperidinecarboxamide | C₆H₁₂N₂O | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-Methoxyphenyl)piperidine-4-carboxamide | C₁₃H₁₈N₂O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 1-(3-Methoxyphenyl)piperidine-4-carboxamide.
Procedure
Copied from the source record, unedited
piperidine-4-carboxamide (0.411 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (6.15 mL, 6.15 mmol) and toluene (10 mL). The resultant mixture was stirred at 100 °C overnight. No sign of reaction by LCMS overnight. Abandoned
The source
This record comes from experimental reaction archive (ord-c91f5415f0604adda8f4b73dd97ab0f8). Open the source and check it against what is on this page.
experimental reaction archive record ord-c91f5415f0604adda8f4b73dd97ab0f8 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.