Buchwald–Hartwig amination, record ord-700c6d20880044119041252f015d9cec
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 | 4-bromo-N,N-dimethylbenzamide | C₉H₁₀BrNO | |
| Reactant | Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1 | C₁₂H₁₃FN₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-[[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-N,N-dimethylbenzamide | C₂₁H₂₂FN₅O | 40.91% |
Conditions
- Temperature
- 120 °C
Yield
- 41% of 4-[[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-N,N-dimethylbenzamide.
Procedure
Copied from the source record, unedited
8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (101 mg, 0.43 mmol), 4-bromo-N,N-dimethylbenzamide (100 mg, 0.44 mmol), Cesium carbonate (211 mg, 0.65 mmol), Palladium(II) acetate (9.8 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (15.8 mg, 0.05 mmol) were added to a microwave vial. The vial was capped and flushed with nitrogen. Dioxane (2.5 mL) was added and the vial was flushed with additional nitrogen before it was irradiated in a microwave reactor at 120 °C for 1.5 h. The reaction mixture was diluted with dichloromethane and filtered through a pad of diatomaceous earth. The pad was rinced repeatedly with dichloromethane, then the solvents were removed _in vacuo_. Handed over to the preparative chromatography group for purification (see attached report
The source
This record comes from experimental reaction archive (ord-700c6d20880044119041252f015d9cec). Open the source and check it against what is on this page.
experimental reaction archive record ord-700c6d20880044119041252f015d9cec 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.