Buchwald–Hartwig amination, record ord-8fdcadcf8d694b72a4ad9ff8119e3e79
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 | 2-Bromo-isonicotinic acid methyl ester | C₇H₆BrNO₂ | |
| Reactant | 4-Fluoro-N-methylaniline | C₇H₈FN | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate | C₁₄H₁₃FN₂O₂ | 0% |
Conditions
- Temperature
- 85 °C
Yield
- 0% of methyl 2-(4-fluoro-N-methylanilino)pyridine-4-carboxylate.
Procedure
Copied from the source record, unedited
In a 100 mL round-bottomed flask (t=g) was biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol), methyl 2-bromoisonicotinate (.1 g, 0.46 mmol), and 4-fluoro-N-methylaniline (0.070 g, 0.56 mmol) in toluene (3 mL) to give a purple suspension. Pd2dba3 (0.021 g, 0.02 mmol) and CS2CO3 (0.211 g, 0.65 mmol) were added. Flask was placed in an oil bath at 85 °C. LC/MS taken at 1, 2 and 4 hours indicated reaction was not progressing. Reaction was discarded.
The source
This record comes from experimental reaction archive (ord-8fdcadcf8d694b72a4ad9ff8119e3e79). Open the source and check it against what is on this page.
experimental reaction archive record ord-8fdcadcf8d694b72a4ad9ff8119e3e79 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.