Buchwald–Hartwig amination, record ord-b9b3987212a34b6286e3f0f13f180d9b
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 | 8-Chloro-4,6-dimethyl-2-(tetrahydrofuran-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₄H₁₉ClN₂O₂ | |
| Reactant | 6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine | C₁₀H₁₂N₄O | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4,6-dimethyl-2-(tetrahydrofuran-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₄H₃₀N₆O₃ | 35.51% |
Conditions
- Temperature
- 100 °C
Yield
- 36% of N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4,6-dimethyl-2-(tetrahydrofuran-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (205 mg, 1.00 mmol), Pd2(dba)3 (22.99 mg, 0.03 mmol), BINAP (31.3 mg, 0.05 mmol) and SODIUM TERT- BUTOXIDE (193 mg, 2.01 mmol) were placed in a round bottomed flask. The flask was stoppered with a septum and flushed with argon. To this was added a solution of 8-chloro-4,6-dimethyl-2-(tetrahydrofuran-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (284 mg, 1.00 mmol) in toluene (5 mL) and the resulting mixture was heated to 100°C for 5 h. The reaction mixture was diluted with dichloromethane and filtered, and the solvent was evaporated. The residue was purified by column chromatography on Silica using gradient elution with increasing concentration of methanol, from 0 to 8 %, in dichloromethane to give a mixture of the two diastereois
The source
This record comes from experimental reaction archive (ord-b9b3987212a34b6286e3f0f13f180d9b). Open the source and check it against what is on this page.
experimental reaction archive record ord-b9b3987212a34b6286e3f0f13f180d9b 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.