Buchwald–Hartwig amination, record ord-8ac590d4cc01454e9f3c19a34317cb92
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 | Benzene, 4-bromo-1,2-dimethoxy- | C₈H₉BrO₂ | |
| Reactant | (R)-1-Boc-2-isopropylpiperazine | C₁₂H₂₄N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | C₂₆H₃₆NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate | C₂₀H₃₂N₂O₄ | 60% |
Conditions
- Temperature
- 150 °C
Yield
- 60% of tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
21-Apr-09 08:58:54 +0100 4-bromo-1,2-dimethoxybenzene (0.135 mL, 0.92 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (252 mg, 1.11 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (10.88 mg, 0.03 mmol) and Sodium tert-butoxide (128 mg, 1.29 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (21.09 mg, 0.02 mmol) were suspended in toluene (5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LC-MS show sproduct at 60% and SM 33% reaction mixture to be combined with EN02263-45 and worked up.
The source
This record comes from experimental reaction archive (ord-8ac590d4cc01454e9f3c19a34317cb92). Open the source and check it against what is on this page.
experimental reaction archive record ord-8ac590d4cc01454e9f3c19a34317cb92 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.