Buchwald–Hartwig amination, record ord-eb19acfe7f704eb2aa769ff5f1767708
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-Chloropyridin-4-yl)methanol | C₆H₆ClNO | |
| Reactant | 4-Fluoro-N-methylaniline | C₇H₈FN | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | [2-(4-fluoro-N-methylanilino)-4-pyridinyl]methanol | C₁₃H₁₃FN₂O | 0% |
Conditions
- Temperature
- 105 °C
Yield
- 0% of [2-(4-fluoro-N-methylanilino)-4-pyridinyl]methanol.
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask (t=g) was (2-chloropyridin-4-yl)methanol (.1 g, 0.70 mmol), Pd2dba3 (0.032 g, 0.03 mmol), and biphenyl-2-yldicyclohexylphosphine (0.024 g, 0.07 mmol) in toluene (6 mL) to give a dark red solution. 4-fluoro-N-methylaniline (0.096 g, 0.77 mmol) and KOtBu (.323 g, 2.88 mmol) were added. Mixture was degassed by bubbling N2 for 20 minutes, then placed in oil bath at 105 °C. Reaction went for 3 hours, at which point LC/MS was taken. No product was observed.
The source
This record comes from experimental reaction archive (ord-eb19acfe7f704eb2aa769ff5f1767708). Open the source and check it against what is on this page.
experimental reaction archive record ord-eb19acfe7f704eb2aa769ff5f1767708 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.