Buchwald–Hartwig amination, record ord-62cd397fe6424e97abf226dd021d8df0
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 | 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one | C₁₂H₁₃N₃O₂ | |
| Reagent | Sodium 2-methylbutan-2-olate | C₅H₁₁NaO | |
| 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 | 5-(2-methoxy-6-(4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)pyridin-3-yl)-1-methylpyridin-2(1H)-one | C₂₃H₂₄F₃N₅O₃ | 26.75% |
Conditions
- Temperature
- 120 °C
Yield
- 27% of 5-(2-methoxy-6-(4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)pyridin-3-yl)-1-methylpyridin-2(1H)-one.
Procedure
Copied from the source record, unedited
A mixture of 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one (0.2 g, 0.86 mmol), 8-chloro-4-methyl-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.243 g, 0.86 mmol), Palladium(II) acetate (0.019 g, 0.09 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (0.050 g, 0.09 mmol) and Sodium tert-pentoxide (0.114 g, 1.04 mmol) in dioxane (1.5 mL) was heated by microwave irradiation to 120 °C for 30 min. The mixture was allowed to cool. DCM (5 mL) was added and the mixture was filtered through a short pad of Celite. The filtrate was collected and the solvent was removed by rotary evaporation. The crude product was added to a silica gel column and was eluted with 0-5% MeOH in DCM. The collected fractions were combined and the solvent was removed by rotary e
The source
This record comes from experimental reaction archive (ord-62cd397fe6424e97abf226dd021d8df0). Open the source and check it against what is on this page.
experimental reaction archive record ord-62cd397fe6424e97abf226dd021d8df0 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.