Buchwald–Hartwig amination, record ord-945adafe269741f9bc504b4e9b38a0a3
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 | (R)-3-Aminopiperidine-2-one | C₅H₁₀N₂O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | O=C1NCCC[C@H]1Nc1ncccc1Cl | C₁₀H₁₂ClN₃O | 2% |
Conditions
- Temperature
- 115 °C
Yield
- 2% of the product.
Procedure
Copied from the source record, unedited
In a 5 ml MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (R)-3-aminopiperidin-2-one (119 mg, 1.04 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 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 over night. The reaction was cooled to rt, DCM and aq NaHCO3 were added, the mixture stirred, filtered through a phase separator and evaporated. LC-MS crude: Traces of product, mainly starting bromide left. Reaction discarded.
The source
This record comes from experimental reaction archive (ord-945adafe269741f9bc504b4e9b38a0a3). Open the source and check it against what is on this page.
experimental reaction archive record ord-945adafe269741f9bc504b4e9b38a0a3 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.