Buchwald–Hartwig amination, record ord-8dc05311ad5340e693477414d5741a5e
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 | O=c1cc(N2CCOCC2)oc2c(-c3ccc(I)c4c3sc3ccccc34)cccc12 | C₂₅H₁₈INO₃S | |
| Reactant | 1-Ethylpiperazine | C₆H₁₄N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 8-[1-(4-Ethylpiperazin-1-yl)dibenzothiophen-4-yl]-2-morpholin-4-ylchromen-4-one | C₃₁H₃₁N₃O₃S | 0% |
Conditions
- Temperature
- 130 °C
Yield
- 0% of 8-[1-(4-Ethylpiperazin-1-yl)dibenzothiophen-4-yl]-2-morpholin-4-ylchromen-4-one.
Procedure
Copied from the source record, unedited
8-(1-iododibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (20 mg, 0.04 mmol), 1-ethylpiperazine (9.42 µl, 0.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.145 mg, 3.71 µmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.849 mg, 0.93 µmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (16.62 µl, 0.11 mmol) were suspended in dioxane (250 µl) and sealed into a microwave tube. The reaction was degased, purged with argon and heated to 130 °C over a period of 45 minutes in the microwave reactor. No reaction.
The source
This record comes from experimental reaction archive (ord-8dc05311ad5340e693477414d5741a5e). Open the source and check it against what is on this page.
experimental reaction archive record ord-8dc05311ad5340e693477414d5741a5e 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.