Buchwald–Hartwig amination: Benzeneacetonitrile, 4-bromo- → 2-[4-[[8-(4-Fluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]acetonitrile
42% 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 | Benzeneacetonitrile, 4-bromo- | C₈H₆BrN | |
| 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 | |
| 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.
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 (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.
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