Buchwald–Hartwig amination, record ord-2bf6474a05bf4e7793ad68ef44642c0b
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-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₁H₁₂ClF₃N₂O | |
| Reactant | 6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine | C₁₀H₁₂N₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₁H₂₃F₃N₆O₂ | 85.35% |
Conditions
- Temperature
- 100 °C
Yield
- 85% of N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
A reaction mixture of 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.044 g, 0.09 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.019 g, 0.09 mmol), Cs2CO3 (0.046 g, 0.14 mmol), Tri-t-butylphosphonium tetrafluoroborate (2.73 mg, 9.41 µmol) and Bis(dibenzylideneacetone)palladium (2.70 mg, 4.70 µmol) in DME (2 mL) was flushed with argon and stirred at rt overnight. No product according to LCMS. The reaction mixture was then run in the microwave at 120°C for 30 minutes. Have unreacted startingmaterial left. Ran the sample again at 120°C for 30 minutes. Doesn´t seem as if the microwave warmed the vial. Added Tri-t-butylphosphonium tetrafluoroborate (2.73 mg, 9.41 µmol) and Bis(dibenzylideneacetone)palladium (2.70 mg, 4.70 µmol) and ra
The source
This record comes from experimental reaction archive (ord-2bf6474a05bf4e7793ad68ef44642c0b). Open the source and check it against what is on this page.
experimental reaction archive record ord-2bf6474a05bf4e7793ad68ef44642c0b 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.