Buchwald–Hartwig amination, record ord-8b74efad6e6646bdaf4fdb6de38026cc
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 | Benzeneacetonitrile, 4-bromo- | C₈H₆BrN | |
| Reactant | Nc1nc2n(n1)CCC[C@@H]2c1ccc(F)cc1 | C₁₂H₁₃FN₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-[4-[[8-(4-Fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]acetonitrile | C₂₀H₁₈FN₅ | 42.09% |
Conditions
- Temperature
- 120 °C
Yield
- 42% of 2-[4-[[8-(4-Fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]acetonitrile.
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 (98 mg, 0.42 mmol), 2-(4-bromophenyl)acetonitrile (83 mg, 0.42 mmol), Cesium carbonate (206 mg, 0.63 mmol), Palladium(II) acetate (9.47 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (14.79 mg, 0.04 mmol) were added to a 2-5 mL microwave vial. The vial was capped and flushed with nitrogen. dioxane (2 mL) was added and the vial was flushed with additional nitrogen before it was heated by microwave irradiation at 120°C for 1.5h. PALLADIUM(II) ACETATE (10 mg, 0.04 mmol) and 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (14 mg, 0.04 mmol) were added and the mixture was heated for 45+30 min at 120° in a microwave reactor.Water (2 ml) and dichloromethane (10 ml) was added and the mixture was added to a phase separator tube. Th
The source
This record comes from experimental reaction archive (ord-8b74efad6e6646bdaf4fdb6de38026cc). Open the source and check it against what is on this page.
experimental reaction archive record ord-8b74efad6e6646bdaf4fdb6de38026cc 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.