Buchwald–Hartwig amination, record ord-c9fc8ca9766b49dfbbd86d67f996e21e
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 | 3-(2-Chloro-5-fluoro-4-pyridinyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine | C₁₂H₁₁ClFN₃ | |
| Reactant | Tert-butyl cis-(3-carbamoylcyclohexyl)carbamate | C₁₂H₂₂N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Tetrakis(triphenylphosphine)palladium | C₇₂H₆₀P₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl N-[(1R,3S)-3-[[5-fluoro-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-2-pyridinyl]carbamoyl]cyclohexyl]carbamate | C₂₄H₃₂FN₅O₃ | 37.41% |
Conditions
- Temperature
- 120 °C
Yield
- 37% of tert-butyl N-[(1R,3S)-3-[[5-fluoro-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-2-pyridinyl]carbamoyl]cyclohexyl]carbamate.
Procedure
Copied from the source record, unedited
Tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (0.200 g, 0.79 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.231 g, 0.95 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.092 g, 0.16 mmol) and Cesium carbonate (0.777 g, 2.38 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 2 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and DCM (40ml) and separated using a phase separation cartridge. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Still impure but telescoped through to
The source
This record comes from experimental reaction archive (ord-c9fc8ca9766b49dfbbd86d67f996e21e). Open the source and check it against what is on this page.
experimental reaction archive record ord-c9fc8ca9766b49dfbbd86d67f996e21e 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.