Buchwald–Hartwig amination, record ord-a5d4f788c47d4d46a04a4c8af6024836
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 | (3-Methyloxetan-3-yl)methanamine | C₅H₁₁NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | CC1(CNc2ncccc2Cl)COC1 | C₁₀H₁₃ClN₂O | 12.22% |
Conditions
- Temperature
- 115 °C
Yield
- 12% of the product.
Procedure
Copied from the source record, unedited
In a 5 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), (3-methyloxetan-3-yl)methanamine (126 mg, 1.25 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 for 1h then to rt for 2h. LC-MS: 61% product, 28% sm left. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 25g column. A gradient from 5% to 50% of EtOAc in heptane over 15CV was used as mobile phase. The product was collected using the wavelength 315 nm, rele
The source
This record comes from experimental reaction archive (ord-a5d4f788c47d4d46a04a4c8af6024836). Open the source and check it against what is on this page.
experimental reaction archive record ord-a5d4f788c47d4d46a04a4c8af6024836 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.