Buchwald–Hartwig amination, record ord-69231428717b458492fb802f1da5509b
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-{5H,6H,7H-pyrrolo[2,1-c][1,2,4]triazol-3-yl}aniline | C₁₁H₁₂N₄ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | (R)-2-(8-(4-(6,7-Dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol | C₂₇H₂₈N₆O₂ | 21.14% |
Conditions
- Temperature
- 100 °C
Yield
- 21% of (R)-2-(8-(4-(6,7-Dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol.
Procedure
Copied from the source record, unedited
4-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)aniline (79 mg, 0.39 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol (120 mg, 0.39 mmol) Palladium acetate (8.84 mg, 0.04 mmol), 2-(Dicyclohexylphosphino)biphenyl (13.80 mg, 0.04 mmol)and Cesium carbonate (385 mg, 1.18 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 crude product was taken up in DCM and the solids were thoroughly washed with DCM. The solvents were evaporated and the crude product was purified on Si. 0-20% MeOH in DCM with 2% triethylamine. Yield: (R)-2-(8-(4-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)phenylamino)-2-phe
The source
This record comes from experimental reaction archive (ord-69231428717b458492fb802f1da5509b). Open the source and check it against what is on this page.
experimental reaction archive record ord-69231428717b458492fb802f1da5509b 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.