Buchwald–Hartwig amination, record ord-ca7fdadedf3340de8e255025b11294fe
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 | 36% |
Conditions
- Temperature
- 150 °C
Yield
- 36% 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 (0.068 mL, 0.46 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (126 mg, 0.55 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (11.21 mg, 0.03 mmol) and Sodium tert-butoxide (63.9 mg, 0.64 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 20 minutes in the microwave reactor and cooled to RT. LC-MS shows 36% product and 57% SM reaction will be combined with EN02263-47
The source
This record comes from experimental reaction archive (ord-ca7fdadedf3340de8e255025b11294fe). Open the source and check it against what is on this page.
experimental reaction archive record ord-ca7fdadedf3340de8e255025b11294fe 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.