Buchwald–Hartwig amination, record ord-b8b79c3ec9d6403bb2571ea1f0499d2f
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-Bromo-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-a)pyridine | C₇H₃BrF₃N₃ | |
| Reactant | 4-[4-[2-(1-methyl-1H-pyrazol-5-yl)ethoxy]phenyl]piperidine | C₁₇H₂₃N₃O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | P-Xylene | C₈H₁₀ | |
| Product | 6-[4-[4-[2-(2-Methylpyrazol-3-yl)ethoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine | C₂₄H₂₅F₃N₆O | 19.14% |
Conditions
- Temperature
- 110 °C
Yield
- 19% of 6-[4-[4-[2-(2-Methylpyrazol-3-yl)ethoxy]phenyl]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine.
Procedure
Copied from the source record, unedited
6-bromo-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (65 mg, 0.24 mmol), 4-(4-(2-(1-methyl-1H-pyrazol-5-yl)ethoxy)phenyl)piperidine (112 mg, 0.24 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (11.41 mg, 0.02 mmol) and Sodium tert-butoxide (0.060 mL, 0.49 mmol) were suspended in xylenes (5 mL), then de-gassed and purged with nitrogen. Bis(dibenzylideneacetone)palladium (7.02 mg, 0.01 mmol) was added, and the mixture was sealed into a microwave tube. The reaction was heated to 110 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (25 mL), and washed with water (25 mL). The aqueous layer was extraced with further EtOAc (25 mL). The combined organic layers were purified by ion exchange chromatography, using an SCX column. Th
The source
This record comes from experimental reaction archive (ord-b8b79c3ec9d6403bb2571ea1f0499d2f). Open the source and check it against what is on this page.
experimental reaction archive record ord-b8b79c3ec9d6403bb2571ea1f0499d2f 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.