Buchwald–Hartwig amination, record ord-c4dfba23f3204e1a90cbbf5ad1b6ca0b
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 | 4-Bromoanisole | C₇H₇BrO | |
| Reactant | 4-Aminomethyltetrahydropyran | C₆H₁₃NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-methoxy-N-(oxan-4-ylmethyl)aniline | C₁₃H₁₉NO₂ | 22.82% |
Conditions
- Temperature
- 80 °C
Yield
- 23% of 4-methoxy-N-(oxan-4-ylmethyl)aniline.
Procedure
Copied from the source record, unedited
Palladium (II) acetate (0.090 g, 0.40 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.464 g, 0.80 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-4-methoxybenzene (1 g, 5.35 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.654 mL, 5.35 mmol) and sodium-t- butoxide (0.771 g, 8.02 mmol) were suspended in toluene (7 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. The mixture was diluted with water (250 mL), and extracted with ethyl acetate (200 mL). The organic was dried over MgSO4, filt
The source
This record comes from experimental reaction archive (ord-c4dfba23f3204e1a90cbbf5ad1b6ca0b). Open the source and check it against what is on this page.
experimental reaction archive record ord-c4dfba23f3204e1a90cbbf5ad1b6ca0b 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.