Buchwald–Hartwig amination, record ord-bcfa3d02b4af4bc4b469f691ad0536a7
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 | 2,6-Dibromopyridine | C₅H₃Br₂N | |
| Reactant | 3-Morpholinone | C₄H₇NO₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-(6-Bromo-2-pyridinyl)morpholin-3-one | C₉H₉BrN₂O₂ | 68.82% |
Conditions
- Temperature
- 80 °C
Yield
- 69% of 4-(6-Bromo-2-pyridinyl)morpholin-3-one.
Procedure
Copied from the source record, unedited
**_September 10 2015_** morpholin-3-one (1g, 9.89 mmol), 2,6-dibromopyridine (3.51 g, 14.84 mmol), PdOAc2 (0.222 g, 0.99 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.145 g, 1.98 mmol) and CS2CO3 (6.12 g, 18.79 mmol) in 1,4-dioxane (20 mL) were heated at 80 °C for 12 hours. **_September 11 2015_** LCMS showed no precursor and 37% of the desired mass MH+ 257/259 @ 0.86 min along with lots of unknowns on a 2-min basic run. The reaction was cooled to RT, and filtered off the solid (Cs2CO3). The filter was concentrated, re-dissolved in EtOAc, washed with waster, dried through MgSO4, and evaporated to give an orange gum. **_September 14 2015_** The orange gum was added to a Biotage column and was eluted with 10-100%EtOAc in Heptane. Collected fractions. The column w
The source
This record comes from experimental reaction archive (ord-bcfa3d02b4af4bc4b469f691ad0536a7). Open the source and check it against what is on this page.
experimental reaction archive record ord-bcfa3d02b4af4bc4b469f691ad0536a7 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.