Buchwald–Hartwig amination, record ord-4ad2f7e2a41645bd9dba54aaef4fa989
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 | 4-(6-Bromo-2-pyridinyl)morpholin-3-one | C₉H₉BrN₂O₂ | |
| Reactant | 2-Amino-4-methylthiazole | C₄H₆N₂S | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one | C₁₃H₁₄N₄O₂S | 80.02% |
Conditions
- Temperature
- 115 °C
Yield
- 80% of 4-[6-[(4-Methyl-1,3-thiazol-2-yl)amino]-2-pyridinyl]morpholin-3-one.
Procedure
Copied from the source record, unedited
**_September 24 2015_** 4-methylthiazol-2-amine (200 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), 4-(6-bromopyridin-2-yl)morpholin-3-one (450 mg, 1.75 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (81 mg, 0.14 mmol) and cesium carbonate (685 mg, 2.10 mmol) in toluene (15 mL) and DMF (1)were microwaved at 115 °C under N2 for one hour. _(Note: Initially, DMF was not added as co-solvent, the microwave instrument was repeatly failed to reach the temperature, and shut down ar 100 °C. It was due to the low thremal absorbance of toluene. Therefore, DMF was added to improve this situation.)_ LCMS showed no precursors and 87% of the desired mass MH+291 @ 0.87 min on a 2-min basic run. The reaction was cooled to RT. **_September 25 2015_** The
The source
This record comes from experimental reaction archive (ord-4ad2f7e2a41645bd9dba54aaef4fa989). Open the source and check it against what is on this page.
experimental reaction archive record ord-4ad2f7e2a41645bd9dba54aaef4fa989 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.