Buchwald–Hartwig amination, record ord-8ca29ea3c13d4e5098dc08cfe112f4d1
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-Bromo-4-nitrotoluene | C₇H₆BrNO₂ | |
| Reactant | 2-Methylquinoline-6-carboxamide | C₁₁H₁₀N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| 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-methyl-N-(2-methyl-5-nitrophenyl)quinoline-6-carboxamide | C₁₈H₁₅N₃O₃ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 2-methyl-N-(2-methyl-5-nitrophenyl)quinoline-6-carboxamide.
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (9.10 mg, 9.94 µmol) was added to 2-bromo-1-methyl-4-nitrobenzene (42.9 mg, 0.20 mmol), 2-methylquinoline-6-carboxamide (37.0 mg, 0.20 mmol), cesium carbonate (194 mg, 0.60 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (11.50 mg, 0.02 mmol) in dioxane (2 mL) at 20°C under nitrogen. The resulting solution was stirred at 100 °C for 6 hours. Reaction seen to be progressing but very sluggish (5% conversion). Reaction abandoned.
The source
This record comes from experimental reaction archive (ord-8ca29ea3c13d4e5098dc08cfe112f4d1). Open the source and check it against what is on this page.
experimental reaction archive record ord-8ca29ea3c13d4e5098dc08cfe112f4d1 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.