Buchwald–Hartwig amination, record ord-05542745a3df403aa88ae927045679bd
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 | 7-Bromo-4-[(2-fluoro-4-methylphenyl)amino]cinnoline-3-carbonitrile | C₁₆H₁₀BrFN₄ | |
| Reactant | Piperazine | C₄H₁₀N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylacetamide | C₄H₉NO | |
| Product | 4-(2-Fluoro-4-methylphenylamino)-7-(piperazin-1-yl)cinnoline-3-carbonitrile | C₂₀H₁₉FN₆ | 84.7% |
Conditions
- Temperature
- 100 °C
Yield
- 85% of 4-(2-Fluoro-4-methylphenylamino)-7-(piperazin-1-yl)cinnoline-3-carbonitrile.
Procedure
Copied from the source record, unedited
A 100 mL flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (0.64 g, 1.79 mmol), Piperazine (0.631 ml, 8.06 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.131 g, 0.14 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso- propyl-1,1'-biphenyl (0.128 g, 0.27 mmol) and Sodium tert-butoxide (0.548 ml, 4.48 mmol). The mixture was suspended in DMA (25.6 ml) and the reaction mixture was stirred at 100 °C for 30min. The reaction mixture was cooled to rt, diluted with DCM/MeOH (10:1) and filtered over a pad of celite. The filterate was concentrated under reduced pressure, adsorbed onto silica gel and flash chromatography using DCM to DCM/MeOH/NH4OH (10:1:0.1) provided the desired compound as a light orange solid.
The source
This record comes from experimental reaction archive (ord-05542745a3df403aa88ae927045679bd). Open the source and check it against what is on this page.
experimental reaction archive record ord-05542745a3df403aa88ae927045679bd 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.