Buchwald–Hartwig amination: 1-Bromo-4-(methylsulphonyl)benzene → tert-butyl (2R)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carboxylate
0% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 1-Bromo-4-(methylsulphonyl)benzene | C₇H₇BrO₂S | |
| Reactant | tert-Butyl (2R)-2-methylpiperazine-1-carboxylate | C₁₀H₂₀N₂O₂ | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(tri-tert-butylphosphine)palladium(0) | C₂₄H₅₄P₂Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl (2R)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carboxylate | C₁₇H₂₆N₂O₄S | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of tert-butyl (2R)-2-methyl-4-(4-methylsulfonylphenyl)piperazine-1-carboxylate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
13-May-09 10:32:28 +0100 1-bromo-4-(methylsulfonyl)benzene (515 mg, 2.13 mmol), (R)-tert-butyl 2-methylpiperazine-1-carboxylate (426 mg, 2.13 mmol) and BIS(TRI-T- BUTYLPHOSPHINE)PALLADIUM(0) (54.3 mg, 0.11 mmol) and potassium 2-methylpropan-2-olate (352 mg, 2.98 mmol) were suspended in dioxane (10 mL) and heated to 90°C for 3 hours. LC-MS shows starting material. Reaction abandoned.
The source
This record comes from experimental reaction archive (ord-8f20cf3b966d4cdd9e1178539b8e969e). Open the source and check it against what is on this page.
experimental reaction archive record ord-8f20cf3b966d4cdd9e1178539b8e969e 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
More Buchwald–Hartwig amination records
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