Buchwald–Hartwig amination, record ord-019ad9f92b5c40ecbf5416e8a6461063
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-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine | C₁₂H₉ClN₄ | |
| Reactant | 1-(6-Amino-5-methoxyindolin-1-yl)ethanone | C₁₁H₁₄N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-[5-Methoxy-6-[(5-methyl-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,3-dihydroindol-1-yl]ethanone | C₂₃H₂₂N₆O₂ | 46.76% |
Conditions
- Temperature
- 90 °C
Yield
- 47% of 1-[5-Methoxy-6-[(5-methyl-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,3-dihydroindol-1-yl]ethanone.
Procedure
Copied from the source record, unedited
A mixture of 3-(2-chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine (400 mg, 1.55 mmol), 1-(6-amino-5-methoxyindolin-1-yl)ethanone (341 mg, 1.55 mmol) and diacetoxypalladium (34.9 mg, 0.16 mmol) 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (97 mg, 0.16 mmol) cesium carbonate (759 mg, 2.33 mmol) were degassed with nitrogen then dioxane (7 mL) was added to mixture and the solution was degassed under vacuum and placed under nitrogen. The resulting suspension was stirred at 90 °C for 5hours. Control uplc/ms OK Control t.l.c : 100%EtOAc and 5%MeOH/CH2Cl2 After cooling, the mixture was filtered and the filtrate evaporated to dryness after addition of silica gel The crude product was purified by flash chromatography on silica gel 45g Merck column solid injectioneluting with 0 to 10%MeOH/Et
The source
This record comes from experimental reaction archive (ord-019ad9f92b5c40ecbf5416e8a6461063). Open the source and check it against what is on this page.
experimental reaction archive record ord-019ad9f92b5c40ecbf5416e8a6461063 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.