Buchwald–Hartwig amination, record ord-870573203c2744a5906bd6a9d998822e
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 | 6-Bromo-1H-indazole | C₇H₅BrN₂ | |
| Reactant | 2-Chloroaniline | C₆H₆ClN | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | N-(2-chlorophenyl)-1H-indazol-6-amine | C₁₃H₁₀ClN₃ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of N-(2-chlorophenyl)-1H-indazol-6-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (0.342 g, 1.52 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (1.422 g, 2.28 mmol) were added to a stirred slurry of 2-chloroaniline (1.763 mL, 16.75 mmol), 6-bromo-1H-indazole (3 g, 15.23 mmol) and cesium carbonate (9.92 g, 30.45 mmol) in toluene (50 mL) at 23°C under nitrogen. The resulting slurry was stirred at 80 °C for 2 hours. The reaction was incomplete (both SM left) so the temperature was increased to 100°C and the reaction mixture was stirred for a further 2 hours. Mainly 2 SM detected. problem of solubility of bromoindazole? The reaction was incomplete and further Palladium(II) acetate (30mg), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (200mg) and cesium carbonate (1g) were added as well as dioxane and the slurry was stirred at 110 °C for
The source
This record comes from experimental reaction archive (ord-870573203c2744a5906bd6a9d998822e). Open the source and check it against what is on this page.
experimental reaction archive record ord-870573203c2744a5906bd6a9d998822e 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.