Buchwald–Hartwig amination, record ord-127ed8ac0e574ba4a6f68accaf8c96d2
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-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine | C₁₄H₁₆ClN₃OS | |
| Reactant | 6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine | C₁₀H₁₂N₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₄H₂₇N₇O₂S | 73.35% |
Conditions
- Temperature
- 110 °C
Yield
- 73% of N-(6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
To 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.086 g, 0.42 mmol) in DME (3 mL) were 8-chloro-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.130 g, 0.42 mmol), cesium carbonate (0.205 g, 0.63 mmol), 2-(Dicyclohexylphosphino)biphenyl (0.015 g, 0.04 mmol) and Palladium acetate (9.42 mg, 0.04 mmol) added. The reaction was heated to 110°C for 60 min under argon atmosphere. The reaction mixture was filtered through celite, washed with DCM and the solvents were evaporated. The crude product was purified by silica flash chromatography, MeOH, 0-5%, in DCM yielding N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-3,4-dimethyl-2-(4-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (0.147 g, 73.4 %). The product was subm
The source
This record comes from experimental reaction archive (ord-127ed8ac0e574ba4a6f68accaf8c96d2). Open the source and check it against what is on this page.
experimental reaction archive record ord-127ed8ac0e574ba4a6f68accaf8c96d2 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.