Buchwald–Hartwig amination: 3,5-Dibromopyridine → 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine
0% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3,5-Dibromopyridine | C₅H₃Br₂N | |
| Reactant | 4-Fluoro-N-methylaniline | C₇H₈FN | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine | C₁₂H₁₀BrFN₂ | 0% |
Conditions
- Temperature
- 110 °C
Yield
- 0% of 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-(Dicyclohexylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | potassium 2-methylpropan-2-olate | Toluene | 110 °C | — | 12% |
| 2-(Dicyclohexylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Toluene | 110 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask (t=g) was 4-fluoro-N-methylaniline (.05 g, 0.40 mmol), 3,5-dibromopyridine (0.114 g, 0.48 mmol), and Pd2(dba)3 (0.018 g, 0.02 mmol) in toluene (16 mL) ([VOLUME]) to give a purple suspension. biphenyl-2-yldicyclohexylphosphine (0.021 g, 0.06 mmol) and CS2CO3 (0.195 g, 0.60 mmol) were added. After LC/MS indicated no reaction had taken place at room temp, the temperature was gradually rasied to up to 110 degrees. LC/MS indicated that the reaction was not progressing. Reaction was discarded.
The source
This record comes from experimental reaction archive (ord-d1bfb220e27441fcb5908d58a9e8690c). Open the source and check it against what is on this page.
experimental reaction archive record ord-d1bfb220e27441fcb5908d58a9e8690c 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.