Buchwald–Hartwig amination, record ord-d99eea842421462c960430aa6c192254
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 | 4-Chlorocinnoline | C₈H₅ClN₂ | |
| Reactant | Cn1ncc(C(=O)N2CCC(N)CC2)c1Cl | C₁₀H₁₅ClN₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | (5-Chloro-1-methyl-pyrazol-4-yl)-[4-(cinnolin-4-ylamino)-1-piperidyl]methanone | C₁₈H₁₉ClN₆O | 8.14% |
Conditions
- Temperature
- 140 °C
Yield
- 8% of (5-Chloro-1-methyl-pyrazol-4-yl)-[4-(cinnolin-4-ylamino)-1-piperidyl]methanone.
Procedure
Copied from the source record, unedited
(4-aminopiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone (442 mg, 1.82 mmol) was taken in a microwave tube. Added racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol) followed by the addition of Palladium (II) acetate (40.9 mg, 0.18 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (113 mg, 0.18 mmol), Cesium carbonate (1782 mg, 5.47 mmol) and diisopropylethyl amine(1ml). toluene (10 mL) was added and stirred at 140 °C for 8h. After the completon of the reaction adsorbed the reaction mass on silica gel and purified by silica gel column.
The source
This record comes from experimental reaction archive (ord-d99eea842421462c960430aa6c192254). Open the source and check it against what is on this page.
experimental reaction archive record ord-d99eea842421462c960430aa6c192254 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.