Buchwald–Hartwig amination, record ord-2b09b0edd9af4f8e80b89621d51beb35
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 | (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine | C₁₅H₁₅ClN₂O | |
| 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 | (R)-5-(2-Methoxy-6-(4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)pyridin-3-yl)-1-methylpyridin-2(1H)-one | C₂₇H₂₇N₅O₃ | 35.11% |
Conditions
- Temperature
- 120 °C
Yield
- 35% of (R)-5-(2-Methoxy-6-(4-methyl-2-phenyl-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
(R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (300 mg, 1.09 mmol), 5-(6-amino-2-methoxypyridin-3-yl)-1-methylpyridin-2(1H)-one (253 mg, 1.09 mmol), Palladium(II) acetate (24.51 mg, 0.11 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (63.2 mg, 0.11 mmol) and Sodium tert-pentoxide (144 mg, 1.31 mmol) were mixed in dioxane (3 mL) and run in a microwave reactor for 40 min at 120°C. the mixture was filtered thru celite and concetrated. purified using flash column chromatography using 0-6 % MeOH (1% NH3) in DCM.
The source
This record comes from experimental reaction archive (ord-2b09b0edd9af4f8e80b89621d51beb35). Open the source and check it against what is on this page.
experimental reaction archive record ord-2b09b0edd9af4f8e80b89621d51beb35 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.