Buchwald–Hartwig amination: (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine → (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine
0% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 4 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine | C₁₅H₁₅ClN₂O | |
| Reactant | 4-(3-Methyl-1H-1,2,4-triazol-1-yl)aniline | C₉H₁₀N₄ | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₄H₂₄N₆O | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Every recorded run making this product
4 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-(Dicyclohexylphosphino)biphenyl; Palladium (II) acetate | Cesium carbonate | 1,2-Dimethoxyethane | 100 °C | — | 0% |
| 2-(Dicyclohexylphosphino)biphenyl; Palladium (II) acetate | potassium 2-methylpropan-2-olate | 1,2-Dimethoxyethane | 100 °C | — | 0% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,2-Dimethoxyethane | 100 °C | — | 0% |
| 2-(Dicyclohexylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | 1,2-Dimethoxyethane | 100 °C | — | 0% |
Procedure
Copied from the source record, unedited
A solution of (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (5.00 mg, 0.02 mmol) and 4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (3.17 mg, 0.02 mmol) in DME (0.5 mL) was added via a syringe to a capped microwave vial containing PALLADIUM(II) ACETATE (0.409 mg, 1.82 µmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.638 mg, 1.82 µmol) and KOtBu (3.06 mg, 0.03 mmol) under an argon atmosphere. The resulting mixture was heated to 100°C in a microwavwe apparatus for 1 h and analyzed by LCMS. No product.
The source
This record comes from experimental reaction archive (ord-22e3f80de08948fdaf8c37b04b642dc6). Open the source and check it against what is on this page.
experimental reaction archive record ord-22e3f80de08948fdaf8c37b04b642dc6 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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