Buchwald–Hartwig amination: 2,6-Dibromopyridine → 4-(6-Bromo-2-pyridinyl)morpholin-3-one
69% yield, run at 80 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.