Buchwald–Hartwig amination, record ord-66ec8d5c98634ce5baad8122520ec3b5
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-3-chloropyridine | C₅H₃BrClN | |
| Reactant | 5-Amino-1-methylpiperidin-2-one | C₆H₁₂N₂O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-[(3-Chloro-2-pyridinyl)amino]-1-methylpiperidin-2-one | C₁₁H₁₄ClN₃O | 0% |
Conditions
- Temperature
- 115 °C
Yield
- 0% of 5-[(3-Chloro-2-pyridinyl)amino]-1-methylpiperidin-2-one.
Procedure
Copied from the source record, unedited
In a 10 ml MW vial, Pd2((dba)3 (10.85 mg, 0.01 mmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (14.56 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (261 mg, 2.71 mmol), 5-amino-1-methylpiperidin-2-one (200 mg, 1.56 mmol) and 2-bromo-3-chloropyridine (300 mg, 1.56 mmol) mixed in toluene (3 mL) to give a brown suspension. The mixture was degassed with N2 bubbling for 5 min, then the vial was capped and the reaction stirred at 115°C in an oil-bath for 1h then to rt for 2h. LC-MS 1h: 15% product. LC-MS o/n: 19% product. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 50g column. A gradient from 20% to 100% of EtOAc in heptane over 20CV was used as mobile phase. The product was collected using the w
The source
This record comes from experimental reaction archive (ord-66ec8d5c98634ce5baad8122520ec3b5). Open the source and check it against what is on this page.
experimental reaction archive record ord-66ec8d5c98634ce5baad8122520ec3b5 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.