Buchwald–Hartwig amination, record ord-89890e81ad5d4e12a61d2ee591f39e46
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 | tert-Butyl 5-bromonicotinate | C₁₀H₁₂BrNO₂ | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-Morpholin-4-yl-nicotinic acid tert-butyl ester | C₁₄H₂₀N₂O₃ | 26.56% |
Conditions
- Temperature
- 80 °C
Yield
- 27% of 5-Morpholin-4-yl-nicotinic acid tert-butyl ester.
Procedure
Copied from the source record, unedited
tert-butyl 5-bromonicotinate (1.4 g, 5.42 mmol), morpholine (0.591 ml, 6.78 mmol), cesium carbonate (3.53 g, 10.85 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.507 g, 0.81 mmol) were dissolved in toluene (20 ml). The reaction flask was purged with nitrogen and diacetoxypalladium (0.061 g, 0.27 mmol) was added. The resulting suspension was stirred at 80 °C for 5 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 5-morpholinonicotinate (0.381 g, 26.6 %) as a yellow oil which solidifi
The source
This record comes from experimental reaction archive (ord-89890e81ad5d4e12a61d2ee591f39e46). Open the source and check it against what is on this page.
experimental reaction archive record ord-89890e81ad5d4e12a61d2ee591f39e46 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.