Buchwald–Hartwig amination, record ord-74a05ca9ab9042dbb66a38d995757deb
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 | 1-[[1-(2-Chloropyrimidin-4-yl)-3-methylpyrazol-4-yl]methyl]azetidin-3-ol | C₁₂H₁₄ClN₅O | |
| Reactant | 3-Chloro-1,2-dimethyl-1H-indol-5-amine | C₁₀H₁₁ClN₂ | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 1-[(1-{2-[(3-Chloro-1,2-Dimethyl-1h-Indol-5-Yl)amino]pyrimidin-4-Yl}-3-Methyl-1h-Pyrazol-4-Yl)methyl]azetidin-3-Ol | C₂₂H₂₄ClN₇O | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 1-[(1-{2-[(3-Chloro-1,2-Dimethyl-1h-Indol-5-Yl)amino]pyrimidin-4-Yl}-3-Methyl-1h-Pyrazol-4-Yl)methyl]azetidin-3-Ol.
Procedure
Copied from the source record, unedited
A 40 mL scintillation vial charged with 3-chloro-1,2-dimethyl-1H-indol-5-amine (53.6 mg, 0.28 mmol), 1-((1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazol-4-yl)methyl)azetidin-3-ol (70mg, 0.25 mmol), palladium(II) acetate (2.81 mg, 0.01 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (x--phos) (11.93 mg, 0.03 mmol) and Dioxane (3 mL) After being degassed by nitrogen bubbling , the reaction mixture was heated to 100 °C for 5 hours. LCMS analysis indicated no desired product and chloropyrimidine starting material was decomposed. The reaction mixture was discarded. Need to reverse the sequence.
The source
This record comes from experimental reaction archive (ord-74a05ca9ab9042dbb66a38d995757deb). Open the source and check it against what is on this page.
experimental reaction archive record ord-74a05ca9ab9042dbb66a38d995757deb 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.