Buchwald–Hartwig amination, record ord-db5f6efbde1f4ab4bc3688dd8d2a4d0e
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 | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | Benzylamine | C₇H₉N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | (R)-(-)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;Ferrocene, 1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)-, (2R)- | C₃₂H₆₂FeP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | N-Benzyl-4-chloropyridin-2-amine | C₁₂H₁₁ClN₂ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of N-Benzyl-4-chloropyridin-2-amine.
Procedure
Copied from the source record, unedited
palladium(II) acetate (0.018 g, 0.08 mmol), (R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T-BUTYLPHOSPHINE (0.066 g, 0.12 mmol), sodium tert-butoxide (0.194 g, 2.02 mmol), phenylmethanamine (0.110 mL, 1.01 mmol) and 2,4-dichloropyridine (0.151 mL, 1.01 mmol) were suspended in DME (4 mL) and sealed into a microwave tube. The reaction was heated to 80 °C for 30 minutes in the microwave reactor and cooled to RT.
The source
This record comes from experimental reaction archive (ord-db5f6efbde1f4ab4bc3688dd8d2a4d0e). Open the source and check it against what is on this page.
experimental reaction archive record ord-db5f6efbde1f4ab4bc3688dd8d2a4d0e 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.