Buchwald–Hartwig amination, record ord-d3bf2a42ca064635a16f6a54a057bf59
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 | (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol | C₁₆H₁₇ClN₂O₂ | |
| Reactant | 3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline | C₁₀H₁₂N₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | (R)-2-(8-(3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol | C₂₆H₂₈N₆O₃ | 21.28% |
Conditions
- Temperature
- 100 °C
Yield
- 21% of (R)-2-(8-(3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol.
Procedure
Copied from the source record, unedited
3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (67.0 mg, 0.33 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (100 mg, 0.33 mmol), Palladium acetate (7.37 mg, 0.03 mmol), 2-(Dicyclohexylphosphino)biphenyl (11.50 mg, 0.03 mmol) and Cesium carbonate (321 mg, 0.98 mmol) were added to a microwave vial. 1,2-dimethoxyethane (2 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 was observed. Additional catalyst and ligand were added and the reaction was run 1h @ 100°C. Still no reaction occurred. EtOH (0.500 mL) was added and another h @ 100°C was executed. Full conversion into product was observed. The solids were filtered off and the solvent was concentrated. The crude
The source
This record comes from experimental reaction archive (ord-d3bf2a42ca064635a16f6a54a057bf59). Open the source and check it against what is on this page.
experimental reaction archive record ord-d3bf2a42ca064635a16f6a54a057bf59 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.