Buchwald–Hartwig amination, record ord-7ce32a5d4abb4826b07e10a8720e8cf8
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 | 3-Bromo-5-methoxypyridine | C₆H₆BrNO | |
| Reactant | 1,4-Dioxa-8-azaspiro(4.5)decane | C₇H₁₃NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 8-(5-Methoxypyridin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane | C₁₃H₁₈N₂O₃ | 75.12% |
Conditions
- Temperature
- 100 °C
Yield
- 75% of 8-(5-Methoxypyridin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane.
Procedure
Copied from the source record, unedited
11/05 2011 07:58:54 +0200 A mixture of 3-bromo-5-methoxypyridine (1.5 g, 7.98 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (1.023 ml, 7.98 mmol), palladium(II) acetate (0.107 g, 0.48 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.228 g, 0.48 mmol) in toluene (38.3 ml) and tBuOH (7.65 ml) was evacuated and flashed with N2 several times. Then sodium 2-methylpropan-2-olate (0.920 g, 9.57 mmol) was added and the reaction mixture was heated to 100°C for 2hrs. LCMS showed complete conversion. Reaction mixture had turned black. The reaction mixture was filtered through celite. The celite was washed with DCM. The combined filtrates were concentrated to yield 2.2g of brown oil, which starts to crystalise patially. Crude NMR showed only little unreacted amine (ca. 14%). The c
The source
This record comes from experimental reaction archive (ord-7ce32a5d4abb4826b07e10a8720e8cf8). Open the source and check it against what is on this page.
experimental reaction archive record ord-7ce32a5d4abb4826b07e10a8720e8cf8 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.