Buchwald–Hartwig amination, record ord-ba7ec5906e7d4fb89a5c2ef7e7a905ac
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 | 5-Chloro-2-nitroanisole | C₇H₆ClNO₃ | |
| Reactant | Tert-butyl 3-oxopiperazine-1-carboxylate | C₉H₁₆N₂O₃ | |
| 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 | Tert-butyl 4-(3-methoxy-4-nitrophenyl)-3-oxopiperazine-1-carboxylate | C₁₆H₂₁N₃O₆ | 100.3% |
Conditions
- Temperature
- 90 °C
Yield
- 100% of Tert-butyl 4-(3-methoxy-4-nitrophenyl)-3-oxopiperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
A mixture of tert-butyl 3-oxopiperazine-1-carboxylate (1500 mg, 7.49 mmol), 4-chloro-2-methoxy-1-nitrobenzene (1405 mg, 7.49 mmol),cesium carbonate (3417 mg, 10.49 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (195 mg, 0.34 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (174 mg, 0.19 mmol)was dried for 15 min under HV. Degassed dioxane (17 ml) was added and the resulting mixture was stirred at 90°C for 16 hours under inert atmosphere. Work-up and purification: see EN02378-07-02. tert-butyl 4-(3-methoxy-4-nitrophenyl)-3-oxopiperazine-1-carboxylate (2640 mg, 100 %) was isolated as an orange foam. FLA 02378-10-01: 1H NMR, LC-MS: OK.
The source
This record comes from experimental reaction archive (ord-ba7ec5906e7d4fb89a5c2ef7e7a905ac). Open the source and check it against what is on this page.
experimental reaction archive record ord-ba7ec5906e7d4fb89a5c2ef7e7a905ac 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.