Buchwald–Hartwig amination, record ord-09c188bd82d940b1aa9d4223b96f551d
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 | Ethyl 7-bromobenzofuran-2-carboxylate | C₁₁H₉BrO₃ | |
| Reactant | 1-(5-(2-(Piperazin-1-yl)ethyl)indolin-1-yl)ethanone | C₁₆H₂₃N₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate | C₂₇H₃₁N₃O₄ | 64.44% |
Conditions
- Temperature
- 95 °C
Yield
- 64% of Ethyl 7-(4-(2-(1-acetylindolin-5-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate.
Procedure
Copied from the source record, unedited
22/04 2009 09:43:42 +0200 To ethyl 7-bromobenzofuran-2-carboxylate (0.095 g, 0.35 mmol) and 1-(5-(2-(piperazin-1-yl)ethyl)indolin-1-yl)ethanone (0.101 g, 0.37 mmol) (from EN02198-74) in dry degassed dioxane (1.5 mL) were added Cesium carbonate (0.150 g, 0.46 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.017 g, 0.04 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.016 g, 0.02 mmol) under argon and the reaction heated at 95°C for 5.5h. After cooling to rt, water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash (SiO2; DCM/MeOH 95/5) to give 0.105 g of the product as a yellow solid.
The source
This record comes from experimental reaction archive (ord-09c188bd82d940b1aa9d4223b96f551d). Open the source and check it against what is on this page.
experimental reaction archive record ord-09c188bd82d940b1aa9d4223b96f551d 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.