Buchwald–Hartwig amination, record ord-fe46b53c9b194686811f12ba6b3f2abb
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-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile | C₁₅H₁₆ClN₅O | |
| Reactant | 4-(2-methyl-1H-imidazol-1-yl)aniline | C₁₀H₁₁N₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 2-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile | C₂₅H₂₆N₈O | 14.26% |
Conditions
- Temperature
- 100 °C
Yield
- 14% of 2-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile.
Procedure
Copied from the source record, unedited
4-(2-methyl-1H-imidazol-1-yl)aniline (0.121 g, 0.70 mmol), Palladium acetate (0.014 g, 0.06 mmol) and Cesium carbonate (0.618 g, 1.90 mmol) were added in a microwave vial. The mixture was capped and flushed with argon. 2-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (0.201 g, 0.63 mmol) in 1,2-dimethoxyethane (5 mL) was added, the reaction mixture was flushed with argon and the mixture was run in a microwave for 60 minutes at 100°C. No product, only unreacted startingmaterial. Added 1 eq CsCO3, and 0.1 eq ligand and palladium acetate, flushed with argon and run in the microwave at 100°C for 60 min. Reaction complete. The reaction mixture was filtrated through Celite and washed with dichloromethane. The filtrate was concentrated and t
The source
This record comes from experimental reaction archive (ord-fe46b53c9b194686811f12ba6b3f2abb). Open the source and check it against what is on this page.
experimental reaction archive record ord-fe46b53c9b194686811f12ba6b3f2abb 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.