Buchwald–Hartwig amination, record ord-decd3260950345c1bc7b269e3329c8ac
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 | 7-Bromo-1-benzofuran | C₈H₅BrO | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate | C₁₇H₂₂N₂O₃ | 84.06% |
Conditions
- Temperature
- 100 °C
Yield
- 84% of Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
7-bromobenzofuran (2 g, 10.15 mmol), tert-Butyl 1-piperazinecarboxylate (1.891 g, 10.15 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.465 g, 0.51 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.484 g, 1.02 mmol) and sodium t-butoxide (1.856 mL, 21.32 mmol) were heated to 100 °C in toluene (10 mL) for 3h. The mixture was allowed to cool to ambient temperature. Ethylacetate was added and the mixture was filtered through Celite. The filtrate was concentrated and redissolved in ethylacetate. The organic mixture was washed with satd. aqueous Na2CO3 and brine. The organic phase was separated, dried over Na2CO3, filtered and the solvent removed by rotary evaporation. The crude product was redissolved in diethylether and loaded onto a silica gel column and eluted with
The source
This record comes from experimental reaction archive (ord-decd3260950345c1bc7b269e3329c8ac). Open the source and check it against what is on this page.
experimental reaction archive record ord-decd3260950345c1bc7b269e3329c8ac 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.