Buchwald–Hartwig amination, record ord-d683d9b583de441b8565719233e1bd75
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 | 1-Bromo-4-phenylmethoxybenzene | C₁₃H₁₁BrO | |
| 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 | Toluene | C₇H₈ | |
| Product | (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)aniline | C₂₂H₃₃NO₂Si | 18.88% |
Conditions
- Temperature
- 120 °C
Yield
- 19% of (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)aniline.
Procedure
Copied from the source record, unedited
Reaction carried out as follows: PdOAc2 (0.768 g, 3.42 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.631 g, 3.42 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromobenzene (9.00 g, 34.20 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (7.77 g, 41.04 mmol) and cesium carbonate (16.72 g, 51.31 mmol) in toluene (200 mL) at 20°C in a 300 ml Milestone microwave reactor. The microwave reactor was sealed and the reaction was heated to 120 °C for 10 hours in and cooled to RT. LCMS indicated some product but mainly sm so another aliquot of catalyst was added and put back on for 10 hours at 130°C. LCMS-2 indicated complete reaction. Handed back to chemist for work-up. Workup The reaction mixture was diluted with EtOAc (100 mL) and was
The source
This record comes from experimental reaction archive (ord-d683d9b583de441b8565719233e1bd75). Open the source and check it against what is on this page.
experimental reaction archive record ord-d683d9b583de441b8565719233e1bd75 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.