Buchwald–Hartwig amination, record ord-8d2093b827454e2d9150258e88282b25
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-phenylmethoxybenzene | C₁₃H₁₁BrO | |
| Reactant | (R)-1-Boc-3-methylpiperazine | C₁₀H₂₀N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | (R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester | C₂₃H₃₀N₂O₃ | 0% |
Conditions
- Temperature
- 150 °C
Yield
- 0% of (R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester.
Procedure
Copied from the source record, unedited
A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.072 g, 0.36 mmol), 1-(benzyloxy)-4-bromobenzene (0.079 g, 0.3 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.035 g, 0.06 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol) and sodium 2-methylpropan-2-olate (0.101 g, 1.05 mmol) in toluene (2 mL) was flushed with nitrogen and sealed into a microwave tube. The reaction was heated to 150 °C for 10 minutes in the microwave reactor and cooled to RT. Only a small amount of the desired product was visible by LCMS. The reaction was not progressed further.
The source
This record comes from experimental reaction archive (ord-8d2093b827454e2d9150258e88282b25). Open the source and check it against what is on this page.
experimental reaction archive record ord-8d2093b827454e2d9150258e88282b25 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.