Buchwald–Hartwig amination, record ord-d91c4f300cee41c898f5dc5506a9a9f7
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-5-fluorobenzotrifluoride | C₇H₃BrF₄ | |
| Reactant | 2-Methylpiperazine, (R)- | C₅H₁₂N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | (R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine | C₁₂H₁₄F₄N₂ | 59% |
Conditions
- Temperature
- 100 °C
Yield
- 59% of (R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine.
Procedure
Copied from the source record, unedited
1-bromo-4-fluoro-2-(trifluoromethyl)benzene (10 g, 41.15 mmol), (R)-2-methylpiperazine (4.33 g, 43.21 mmol), sodium tert-butoxide (7.91 g, 82.31 mmol) and BINAP (1.025 g, 1.65 mmol) in anhydrous toluene (100 mL) was degassed under vacuum with inlet of nitrogen. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.754 g, 0.82 mmol) was added, the mixture again degassed. The resulting suspension was stirred at 100 °C for 4 hours under nitrogen. LCMS: Product formed. Heated for a further 2 hours. LCMS: Reaction complete. Cooled and evaporated. Residue diluted with diethyl ether (75 mL), filtered through Celite and the filtrates extracted with 2M HCl (2x30 mL). The combined aqueous layers were basified with solid NaOH to pH ~10, extracted with diethyl ether (2x50 mL), the organic extracts washed wi
The source
This record comes from experimental reaction archive (ord-d91c4f300cee41c898f5dc5506a9a9f7). Open the source and check it against what is on this page.
experimental reaction archive record ord-d91c4f300cee41c898f5dc5506a9a9f7 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.