Buchwald–Hartwig amination, record ord-7c9ead47a3324fac997f2b8af6afca02
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 | 2,6-Dichloroisonicotinic acid | C₆H₃Cl₂NO₂ | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid | C₁₁H₁₃ClN₂O₄ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid.
Procedure
Copied from the source record, unedited
Reagents were mixed in a 25 mL round bottom flask and flushed well with nitrogen - heated at 100 °C for 16 h. The mixture looked dark black. Could not detect any starting material or product! It was discarded.
The source
This record comes from experimental reaction archive (ord-7c9ead47a3324fac997f2b8af6afca02). Open the source and check it against what is on this page.
experimental reaction archive record ord-7c9ead47a3324fac997f2b8af6afca02 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.