Buchwald–Hartwig amination: 3-Bromo-2,6-dichloropyridine → 4-(2,6-Dichloro-3-pyridinyl)morpholine
0% yield, run at 25 °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 | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl | C₃₀H₄₃O₂P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | tert-Butanol | C₄H₁₀O | |
| Product | 4-(2,6-Dichloro-3-pyridinyl)morpholine | C₉H₁₀Cl₂N₂O | 0% |
Conditions
- Temperature
- 25 °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% (this run) |
| 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Tetrahydrofuran | 100 °C | — | 0% |
Procedure
Copied from the source record, unedited
2011-05-18 r1 was checked by NMR and LC/MS: Vial a: 3-bromo-2,6-dichloropyridine (0.023 g, .1 mmol), morpholine (9.15 µl, 0.11 mmol), Pd2dba3 (1.831 mg, 2.00 µmol),4-(2,6-dichloropyridin-3-yl)morpholine (0.00 µg) were mixed in tBuOH (0.241 ml) in microwave vial. The vial was flushed with N2 and sealed and the mix was strd at rt. Vial b: As above, but in PhCF3. 1100:start 2011-05-19 0800: LC/MS: around 50% r1 in both vials. vial a: new peak at 1.53 min (20%), at 2.90 min (17%) and some small peaks as well. vial b: new peak at 1.54 min (32%), 2.61 min (25%) and at 2.90 min (5%) and some small peaks as well. MW/100 degr/20 min. LC/MS, pH3: vial a: 1.17 min: new peak (8-9%, not integrated); 2.11 min: new peak (31%), no right mass track. vial b: 1.17 min: new, small peak; 2.11 min:
The source
This record comes from experimental reaction archive (ord-b1c7bfb9b1414262b689b975ba465d86). Open the source and check it against what is on this page.
experimental reaction archive record ord-b1c7bfb9b1414262b689b975ba465d86 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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