Buchwald–Hartwig amination, record ord-775ba0e2a4c14f008f392711cc2a587a
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 | 3,5-Dibromo-1-methyl-1H-1,2,4-triazole | C₃H₃Br₂N₃ | |
| Reactant | 1-Methylpiperazine | C₅H₁₂N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)-4-methylpiperazine | C₈H₁₄BrN₅ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 1-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)-4-methylpiperazine.
Procedure
Copied from the source record, unedited
A mixture of 3,5-dibromo-1-methyl-1H-1,2,4-triazole (142 mg, 0.59 mmol), 1-methylpiperazine (62.0 mg, 0.62 mmol), tris(dibenzylideneacetone)dipalladium(0) (81 mg, 0.09 mmol), BINAP (110 mg, 0.18 mmol) and sodium tert-butoxide (113 mg, 1.18 mmol) in toluene (8 ml) was stirred at 100 °C for 1.5hrs. LCMS indicated no desired product formation. Discarded.
The source
This record comes from experimental reaction archive (ord-775ba0e2a4c14f008f392711cc2a587a). Open the source and check it against what is on this page.
experimental reaction archive record ord-775ba0e2a4c14f008f392711cc2a587a 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.