Buchwald–Hartwig amination, record ord-a50a848eea9042a19d3b9efbefd39662
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 | Methyl 4-bromobenzoate | C₈H₇BrO₂ | |
| Reactant | 3,5-Difluorobenzylamine | C₇H₇F₂N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 4-[(3,5-difluorophenyl)methylamino]benzoate | C₁₅H₁₃F₂NO₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of Methyl 4-[(3,5-difluorophenyl)methylamino]benzoate.
Procedure
Copied from the source record, unedited
methyl 4-bromobenzoate (1.8 g, 8.37 mmol), (3,5-difluorophenyl)methanamine (1.980 mL, 16.74 mmol) and Cesium carbonate (2.73 g, 8.37 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (0.094 g, 0.42 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.365 g, 0.59 mmol) were added and the vial was capped and heated at 100°C over 5 days. Workup by dilution with EtOAc, washing with water, then extraction with 2M HCl. The HCl extract was neutralized with 2M NaOH and extracted with EtOAc and the EtOAc phase was dried (K2CO3) and evaporated to give the crude product. The desired amine was not the compound isolated. Discarded.
The source
This record comes from experimental reaction archive (ord-a50a848eea9042a19d3b9efbefd39662). Open the source and check it against what is on this page.
experimental reaction archive record ord-a50a848eea9042a19d3b9efbefd39662 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.