Buchwald–Hartwig amination: 1-Bromo-4-phenylmethoxybenzene → (R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester
0% yield, run at 150 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
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 | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| 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.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| Tris(1,1-dimethylethyl)phosphine; Bis(tri-tert-butylphosphine)palladium(0) | potassium 2-methylpropan-2-olate | Tetrahydrofuran | 75 °C | — | 32% |
| Binap, (A+-)-; Palladium (II) acetate | sodium 2-methylpropan-2-olate | Toluene | 150 °C | — | 0% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Toluene | 150 °C | — | 0% |
Procedure
Copied from the source record, unedited
A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.060 g, 0.3 mmol), 1-(benzyloxy)-4-bromobenzene (0.095 g, 0.36 mmol), palladium(II) acetate (6.74 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.015 g, 0.02 mmol) and sodium t-butoxide (0.043 g, 0.45 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. Analysis by LCMS. Only a small amount of the product could be detected (MH+ = 383, 5%). The reaction was not progressed further.
The source
This record comes from experimental reaction archive (ord-aba439bdbf614f12a2c2928a8b3049c5). Open the source and check it against what is on this page.
experimental reaction archive record ord-aba439bdbf614f12a2c2928a8b3049c5 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.
Where to next
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