Buchwald–Hartwig amination, record ord-be476d7266d0479ba1e6c4f9e5b26400
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 | tert-Butyl (2-(3-bromo-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)-2-oxoethyl)carbamate | C₂₁H₂₆BrFN₄O₃ | |
| Reactant | 4-Fluoroaniline | C₆H₆FN | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Carbamic acid, N-[2-[2-(4-fluorophenyl)-3-[(4-fluorophenyl)amino]-5,6-dihydro-8,8-dimethylimidazo[1,2-a]pyrazin-7(8H)-yl]-2-oxoethyl]-, 1,1-dimethylethyl ester | C₂₇H₃₁F₂N₅O₃ | 83.27% |
Conditions
- Temperature
- 120 °C
Yield
- 83% of Carbamic acid, N-[2-[2-(4-fluorophenyl)-3-[(4-fluorophenyl)amino]-5,6-dihydro-8,8-dimethylimidazo[1,2-a]pyrazin-7(8H)-yl]-2-oxoethyl]-, 1,1-dimethylethyl ester.
Procedure
Copied from the source record, unedited
In a microwave vial, cesium carbonate (135 mg, 0.42 mmol), 4-fluoroaniline (92 mg, 0.83 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.02 mg, 0.02 mmol), Xantphos (24.04 mg, 0.04 mmol) and dry 1,4-dioxane (6 mL) were stirred for 5 minutes at room temperature. tert-butyl (2-(3-bromo-2-(4-fluorophenyl)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)-2-oxoethyl)carbamate (200 mg, 0.42 mmol) was added to the reaction mixture after which the reaction mixture was degassed for 15 mins and then stirred at 120 °C under N2 for 20 h. The reaction was monitored by LCMS. The profile showed formation of title product. The reaction mixture was filtered through a pad opf celite and the filtrate was concentrated to give a residue. The residue was purified by silica gel followed by reverse
The source
This record comes from experimental reaction archive (ord-be476d7266d0479ba1e6c4f9e5b26400). Open the source and check it against what is on this page.
experimental reaction archive record ord-be476d7266d0479ba1e6c4f9e5b26400 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.