Buchwald–Hartwig amination, record ord-ce627b9c98e74957a0959e5bb6499f88
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 | 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one | C₉H₈BrNO | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate | C₁₈H₂₅N₃O₃ | 57.03% |
Conditions
- Temperature
- 60 °C
Yield
- 57% of tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
In an oven-dried RB flask was added Tris(dibenzylideneacetone)dipalladium(0) (0.046 g, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.062 g, 0.10 mmol). The flask was evacuated and back-filled with nitrogen. Anhydrous toluene (3 mL) was added and the mixture was stirred at rt for 10 min to give a purple solution. 6-bromo-2-methylisoindolin-1-one (2.261 g, 10 mmol), 1-Boc-piperazine (1.863 g, 10.00 mmol) and Sodium tert-butoxide (1.714 mL, 14.00 mmol) were added in one portion followed by anhydrous toluene (15 mL). The flask was evacuated and back-filled with nitrogen and the resulting mixture was stirred at 60 °C under a nitrogen atmosphere for 2 days. LCMS shows 10% conversion. Tris(dibenzylideneacetone)dipalladium(0) (0.183 g, 0.20 mmol) and 2-Dicyclohexylphosphino-2',
The source
This record comes from experimental reaction archive (ord-ce627b9c98e74957a0959e5bb6499f88). Open the source and check it against what is on this page.
experimental reaction archive record ord-ce627b9c98e74957a0959e5bb6499f88 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.