Buchwald–Hartwig amination, record ord-e4f50ecc5cb146dc9c3dbbd5fbb158a0
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 | 5-Bromo-2-chloro-4-methylpyridine | C₆H₅BrClN | |
| Reactant | Ethyl 4-piperidinecarboxylate | C₈H₁₅NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | CCOC(=O)C1CCN(c2cnc(Cl)cc2C)CC1 | C₁₄H₁₉ClN₂O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of the product.
Procedure
Copied from the source record, unedited
A solution of diacetoxypalladium (10.87 mg, 0.05 mmol) and dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine (45.2 mg, 0.10 mmol) dissolved in toluene (3 mL) was degassed and heated to 50°C for 30 minutes before adding ethyl piperidine-4-carboxylate (0.105 mL, 0.68 mmol), 5-bromo-2-chloro-4-methylpyridine (100 mg, 0.48 mmol) and sodium 2-methylpropan-2-olate (74.5 mg, 0.77 mmol) under nitrogen. The mixture was heated to 100°C for 2 hours. LCMS indicated little product so reaction abandoned.
The source
This record comes from experimental reaction archive (ord-e4f50ecc5cb146dc9c3dbbd5fbb158a0). Open the source and check it against what is on this page.
experimental reaction archive record ord-e4f50ecc5cb146dc9c3dbbd5fbb158a0 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.