Buchwald–Hartwig amination, record ord-2d4104aef43247ff855d465ce3910528
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 | 6-chloro-N-cyclohexylpyridine-3-carboxamide | C₁₂H₁₅ClN₂O | |
| Reactant | 4-Aminobenzonitrile | C₇H₆N₂ | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | N#Cc1ccc(Nc2ccc(C(=O)NC3CCCCC3)cn2)cc1 | C₁₉H₂₀N₄O | 9.93% |
Conditions
- Temperature
- 100 °C
Yield
- 10% of the product.
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask a TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.115 g, 0.13 mmol),POTASSIUM TERT-BUTOXIDE (0.282 g, 2.51 mmol)and BINAP (0.157 g, 0.25 mmol) in dry 1,4-dioxane (10 mL) was mixed under N2.Followed by 6-chloro-N-cyclohexylnicotinamide (.300 g, 1.26 mmol) and 4-aminobenzonitrile (0.178 g, 1.51 mmol) was added and resulting mixture(dark brown) was heated at 100oC for 3 hrs.LCMS analysis showed the formation of required product.Reaction stopped,crude was passed through celite and washed with dioxane and finally with methanol.The filtrate was dried and dissolved in 3 ml DMSO for Waters MS Purification system.Pure fractions collected and concentrated.A White solid obtained as a product 6-(4-cyanophenylamino)-N-cyclohexylnicotinamide (0.040 g, 9.93 %).32 mg of above p
The source
This record comes from experimental reaction archive (ord-2d4104aef43247ff855d465ce3910528). Open the source and check it against what is on this page.
experimental reaction archive record ord-2d4104aef43247ff855d465ce3910528 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.