Buchwald–Hartwig amination: 4-Bromo-2-nitroanisole → 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone
0% yield, run at 80 °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 | 4-Bromo-2-nitroanisole | C₇H₆BrNO₃ | |
| Reactant | 1-(9-Oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethan-1-one | C₈H₁₄N₂O₂ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone | C₁₅H₁₉N₃O₅ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of 1-(7-(4-Methoxy-3-nitrophenyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone.
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)biphenyl; Palladium (II) acetate | Potassium Phosphate, Tribasic | 1,2-Dimethoxyethane | 80 °C | — | 0% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | sodium 2-methylpropan-2-olate | 1,4-Dioxane | 110 °C | — | 0% |
Procedure
Copied from the source record, unedited
1-(9-oxa-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone (36.3 mg, 0.21 mmol), 4-bromo-1-methoxy-2-nitrobenzene (45 mg, 0.19 mmol), diacetoxypalladium (4.35 mg, 0.02 mmol), biphenyl-2-yldicyclohexylphosphine (10.88 mg, 0.03 mmol) and potassium phosphate (61.8 mg, 0.29 mmol) in DME (0.5 mL) were degassed with nitrogen and stirred at 80 °C overnight => _no product formed, degradation_ **_ABANDONED_**
The source
This record comes from experimental reaction archive (ord-e6979ae841a4470289e0e5d2e2b42616). Open the source and check it against what is on this page.
experimental reaction archive record ord-e6979ae841a4470289e0e5d2e2b42616 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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