Buchwald–Hartwig amination, record ord-7d01f29fd6fc44f08392db2774553827
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 | 4-Amino-2-methoxybenzonitrile | C₈H₈N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | (R)-4-(4-(2-Hydroxyethyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)-2-methoxybenzonitrile | C₂₄H₂₄N₄O₃ | 13.17% |
Conditions
- Temperature
- 100 °C
Yield
- 13% of (R)-4-(4-(2-Hydroxyethyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)-2-methoxybenzonitrile.
Procedure
Copied from the source record, unedited
4-amino-2-methoxybenzonitrile (72.9 mg, 0.49 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (150 mg, 0.49 mmol), Palladium acetate (11.05 mg, 0.05 mmol), 2-(Dicyclohexylphosphino)biphenyl (17.25 mg, 0.05 mmol)and Cesium carbonate (481 mg, 1.48 mmol) were added to a microwave vial. 1,2-dimethoxyethane (2 mL) and EtOH (0.500 mL) were added. The reaction mixture was flushed with argon and the mixture was run in a microwave for 60 minutes at 100°C. The solvent was decanted and the solids were washed with 5ml DCM. The solvent was evaporated and the crude product was purified on Si, 0-6% MeOH in DCM, yielding (R)-4-(4-(2-hydroxyethyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)-2-methoxybenzonitrile (27.0 mg, 13.17 %)
The source
This record comes from experimental reaction archive (ord-7d01f29fd6fc44f08392db2774553827). Open the source and check it against what is on this page.
experimental reaction archive record ord-7d01f29fd6fc44f08392db2774553827 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.