Buchwald–Hartwig amination, record ord-48707410a8f646d7ad65813e3cef2505
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-(methyloxy)benzamide | C₁₃H₁₁Cl₂N₃O₂ | |
| Reactant | 1,3-dimethyl-1H-pyrazol-4-amine | C₅H₉N₃ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-({5-Chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)-amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide | C₁₈H₁₉ClN₆O₂ | 14.3% |
Conditions
- Temperature
- 150 °C
Yield
- 14% of 2-({5-Chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)-amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide.
Procedure
Copied from the source record, unedited
2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (250 mg, 0.80 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol), Sodium tert-butoxide (115 mg, 1.20 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol) and BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) were suspended in dioxane (15 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. Reaction not complete by LCMS so more 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol), BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) and 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol) were added and the reaction heated to 150 ºC for a further 30 minutes in the microwave reactor and cooled to RT.
The source
This record comes from experimental reaction archive (ord-48707410a8f646d7ad65813e3cef2505). Open the source and check it against what is on this page.
experimental reaction archive record ord-48707410a8f646d7ad65813e3cef2505 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.