Buchwald–Hartwig amination, record ord-76b900b67381471d89fef9247f442cb0
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 | 1-Bromo-4-iodobenzene | C₆H₄BrI | |
| Reactant | rel-(2R,6S)-2,6-dimethylpiperazine | C₆H₁₄N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-(4-Bromophenyl)-cis-3,5-dimethylpiperazine | C₁₂H₁₇BrN₂ | 61.61% |
Conditions
- Temperature
- 90 °C
Yield
- 62% of 1-(4-Bromophenyl)-cis-3,5-dimethylpiperazine.
Procedure
Copied from the source record, unedited
sodium 2-methylpropan-2-olate (4.08 g, 42.42 mmol) was added to (2R,6S)-2,6-dimethylpiperazine (4.84 g, 42.42 mmol) in dioxane (300 mL) at 21°C under nitrogen. Stirred for 5 mins. 1-bromo-4-iodobenzene (8 g, 28.28 mmol) added, followed by diacetoxypalladium (0.635 g, 2.83 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (3.27 g, 5.66 mmol). Reaction evacuated and refilled with nitrogen several times. Heated at 90C for 18hours. Diluted with ethyl acetate and filtered through celite. The organic layer was washed with water ( 500ml) and then dried over Na2SO4, filtered and reduced in volume. Filtered - lcms messy. Dissolved in DCM and combined with the filtrate - adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 30%
The source
This record comes from experimental reaction archive (ord-76b900b67381471d89fef9247f442cb0). Open the source and check it against what is on this page.
experimental reaction archive record ord-76b900b67381471d89fef9247f442cb0 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.