Buchwald–Hartwig amination: 1-(Benzyloxy)-4-bromo-2-fluorobenzene → (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)-3-fluoroaniline
0% yield, run at 120 °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 | 1-(Benzyloxy)-4-bromo-2-fluorobenzene | C₁₃H₁₀BrFO | |
| Reactant | (R)-2-(tert-butyldimethylsilyloxy)propan-1-amine | C₉H₂₃NOSi | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)-3-fluoroaniline | C₂₂H₃₂FNO₂Si | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)-3-fluoroaniline.
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',4',6'-triisoprophylbiphenyl; Palladium (II) acetate | Cesium carbonate | Toluene | 120 °C | — | 65% |
| 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl; Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 120 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
PdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1 g, 3.56 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.808 g, 4.27 mmol) and cesium carbonate (1.739 g, 5.34 mmol) in anhydrous dioxane (20 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 10 hours in the microwave reactor and cooled to RT. LCMS indicates mainly starting material **** No further action was taken.
The source
This record comes from experimental reaction archive (ord-1df10534bfeb467c9df72e530f4b3ab2). Open the source and check it against what is on this page.
experimental reaction archive record ord-1df10534bfeb467c9df72e530f4b3ab2 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
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