Buchwald–Hartwig amination: 2-(4-bromophenyl)-N,N-dimethylacetamide → 2-[4-[[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-N,N-dimethylacetamide
32% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-(4-bromophenyl)-N,N-dimethylacetamide | C₁₀H₁₂BrNO | |
| Reactant | (8R)-8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine | C₁₂H₁₃FN₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| 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]-N,N-dimethylacetamide | C₂₂H₂₄FN₅O | 32.03% |
Conditions
- Temperature
- 120 °C
Yield
- 32% of 2-[4-[[8-(4-fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-N,N-dimethylacetamide.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
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 (94 mg, 0.40 mmol), 2-(4-bromophenyl)-N,N-dimethylacetamide (103 mg, 0.40 mmol), Cesium carbonate (198 mg, 0.61 mmol), Palladium(II) acetate (9.09 mg, 0.04 mmol) and 2-(Dicyclohexylphosphino)biphenyl (14.18 mg, 0.04 mmol) were added to a 0.5-2 mL microwave vial. The vial was capped and flushed with nitrogen. dioxane (3 mL) was added and the vial was flushed with additional nitrogen before it was heated by microwave irradiation at 120°C for 1.5h. The reaction mixture was cooled to r.t. and water and EtOAc were added and the layers were separated. The aqueous phase was extracted with EtOAc (3x). The combined organic phases were washed with brine, dried (phase separator) and the solvent was removed under reduced pres
The source
This record comes from experimental reaction archive (ord-31e2f0a986f6432689bfa64e01da3c0f). Open the source and check it against what is on this page.
experimental reaction archive record ord-31e2f0a986f6432689bfa64e01da3c0f 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.
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