Buchwald–Hartwig amination: 3-Bromo-2,6-dichloropyridine → 4-(2,6-Dichloro-3-pyridinyl)morpholine
0% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromo-2,6-dichloropyridine | C₅H₂BrCl₂N | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | 4-(2,6-Dichloro-3-pyridinyl)morpholine | C₉H₁₀Cl₂N₂O | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 4-(2,6-Dichloro-3-pyridinyl)morpholine.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | tert-Butanol | 25 °C | — | 0% |
| 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Tetrahydrofuran | 100 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
sodium tert-butoxide (0.012 g, 0.13 mmol), were transfered to a microwave vial. Pd2dba3 (0.916 mg, 1.00 µmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.933 mg, 2.00 µmol), (2-DICYCLOHEXYLPHOSPHINO-2',6'-DIISOPROPYL-1,1'-BIPHENYL)[2-(2-AMINOETHYL)PHENYL]PALLADIUM(II) (0.729 mg, 1.00 µmol) were added. 3-bromo-2,6-dichloropyridine (0.011 g, .05 mmol) in tetrahydrofuran (0.474 ml) was added. The vial was flushed with N2, sealed, and the reaction mix was heated on an oil bath at 100 °C. 2011-10-05 0900: interrupted, cooled- LC/MS, 5 min method, pH11: 1H NMR on crude:not good spectra. 2011-10-06 The mix was filtered thru Si-plug and conc. 1H NMR and COSY. Very complex. Lower rection temp and time needed. Discarded. \---- Info from -25: 2011-09-18 Lit. ref: ....B
The source
This record comes from experimental reaction archive (ord-7a326b6af66842839478f845f091880c). Open the source and check it against what is on this page.
experimental reaction archive record ord-7a326b6af66842839478f845f091880c 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.
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