Buchwald–Hartwig amination, record ord-bf7cf9ac04cd4fedb1f93e4a263e0d2f
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 | 2-Chloro-8-(3,3-difluoro-cyclobutyl)-6-methyl-5,6,7,8-tetrahydro-9-oxa-1,6-diaza-benzocycloheptene | C₁₃H₁₅ClF₂N₂O | |
| Reactant | 6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine | C₁₀H₁₂N₄O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-(3,3-Difluorocyclobutyl)-N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine | C₂₃H₂₆F₂N₆O₂ | 69.57% |
Conditions
- Temperature
- 145 °C
Yield
- 70% of 2-(3,3-Difluorocyclobutyl)-N-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine.
Procedure
Copied from the source record, unedited
Palladium(II) acetate (0.019 g, 0.08 mmol) and 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.096 g, 0.17 mmol) were added to a degassed solution of 8-chloro-2-(3,3-difluorocyclobutyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.160 g, 0.55 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.113 g, 0.55 mmol) and Cesium carbonate (0.058 mL, 0.72 mmol) in dry dioxane (15 mL). The reaction was heated in a microwave oven at 145°C for 1h. About 50% of product. The reaction was heated at 145°C for another 30 min. About 45% of product. The reaction was interrupted and the reaction mixture was pooled with the corresponding mixture in EN04426-52. The reaction mixture was filtered through a plug of celite. The celite was washed with DCM. The solvents were evaporated an
The source
This record comes from experimental reaction archive (ord-bf7cf9ac04cd4fedb1f93e4a263e0d2f). Open the source and check it against what is on this page.
experimental reaction archive record ord-bf7cf9ac04cd4fedb1f93e4a263e0d2f 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.