Buchwald–Hartwig amination, record ord-23579b28ef824d8ba8083ac0e9a7b70a
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 | 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide | C₁₃H₁₁Cl₂N₃O | |
| Reactant | 1,3-dimethyl-1H-pyrazol-4-amine | C₅H₉N₃ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)- | C₃₂H₆₂FeP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 2-({5-Chloro-2-[(1,3-dimethyl-1h-pyrazol-4-yl)amino]-4-pyridinyl}amino)-n-methylbenzamide | C₁₈H₁₉ClN₆O | 53.31% |
Conditions
- Temperature
- 150 °C
Yield
- 53% of 2-({5-Chloro-2-[(1,3-dimethyl-1h-pyrazol-4-yl)amino]-4-pyridinyl}amino)-n-methylbenzamide.
Procedure
Copied from the source record, unedited
1,3-dimethyl-1H-pyrazol-4-amine (180 mg, 1.62 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (400 mg, 1.35 mmol), Sodium t-Butoxide (156 mg, 1.62 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (73.8 mg, 0.14 mmol) and diacetoxypalladium (24.26 mg, 0.11 mmol) were suspended in DME (8 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Incomplete reaction, the reaction was heated to 150 °C for a further 1 hour in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was then p
The source
This record comes from experimental reaction archive (ord-23579b28ef824d8ba8083ac0e9a7b70a). Open the source and check it against what is on this page.
experimental reaction archive record ord-23579b28ef824d8ba8083ac0e9a7b70a 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.