Buchwald–Hartwig amination, record ord-8563d32d81ef4e67b37807469f34e85c
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)-5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazole | C₁₃H₁₃ClFN₃ | |
| 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-[[4-(5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate | C₂₅H₃₄FN₅O₃ | 35.11% |
Conditions
- Temperature
- 120 °C
Yield
- 35% of tert-butyl N-[(1R,3S)-3-[[4-(5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate.
Procedure
Copied from the source record, unedited
Tetrakis(triphenylphosphine)palladium(0) (56.5 mg, 0.05 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (130 mg, 0.49 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (119 mg, 0.49 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (56.6 mg, 0.10 mmol) and Cesium carbonate (478 mg, 1.47 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. Pure fractions were evaporated t
The source
This record comes from experimental reaction archive (ord-8563d32d81ef4e67b37807469f34e85c). Open the source and check it against what is on this page.
experimental reaction archive record ord-8563d32d81ef4e67b37807469f34e85c 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.