Buchwald–Hartwig amination, record ord-15613520ef9b4d099659a0a3ac545228
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 | 4-Bromopyridine | C₅H₄BrN | |
| Reactant | 4-Hydroxypyrrolidine | C₄H₉NO | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | C₂₆H₃₆NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | 1-(Pyridin-4-yl)pyrrolidin-3-ol | C₉H₁₂N₂O | 43.01% |
Conditions
- Temperature
- 65 °C
Yield
- 43% of 1-(Pyridin-4-yl)pyrrolidin-3-ol.
Procedure
Copied from the source record, unedited
In a 50 ml round bottomed flask THF (1 mL) was added to a mixture of 4-bromopyridine (1 g, 6.33 mmol), pyrrolidin-3-ol (0.662 g, 7.60 mmol),2-(dimethylamino)-2'-(dicyclohexylphosphino)biphenyl (0.249 g, 0.63 mmol) and Pd2(dba)3 (0.580 g, 0.63 mmol). To the slurry lithium bis(trimethylsilyl)amide (13.92 mL, 13.92 mmol) was added dropwise at 0 °C and the solution was refluxed at 65 °C overnight for 20 hrs. The reaction mixture was passed through celite, concentrated and column purified (0-20%MeOH/DCM) to obtain 0.447 mg of product.
The source
This record comes from experimental reaction archive (ord-15613520ef9b4d099659a0a3ac545228). Open the source and check it against what is on this page.
experimental reaction archive record ord-15613520ef9b4d099659a0a3ac545228 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.