Buchwald–Hartwig amination: Benzene, 1-bromo-3-iodo- → 3-Bromo-N-[(oxan-4-yl)methyl]aniline
31% yield, run at 80 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Benzene, 1-bromo-3-iodo- | C₆H₄BrI | |
| Reactant | 4-Aminomethyltetrahydropyran | C₆H₁₃NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 3-Bromo-N-[(oxan-4-yl)methyl]aniline | C₁₂H₁₆BrNO | 30.98% |
Conditions
- Temperature
- 80 °C
Yield
- 31% of 3-Bromo-N-[(oxan-4-yl)methyl]aniline.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
Palladium (II) acetate (14.28 mg, 0.06 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (79 mg, 0.13 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-3-iodobenzene (240 mg, 0.85 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (98 mg, 0.85 mmol) and sodium-t-butoxide (122 mg, 1.27 mmol) were suspended in toluene (3.5 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. This reaction was combined with EN06953-06 for purification. The mixture was filtered and purified by flash silica chromatography, el
The source
This record comes from experimental reaction archive (ord-ff2be4fb066f4702ab3412c6fd0e670a). Open the source and check it against what is on this page.
experimental reaction archive record ord-ff2be4fb066f4702ab3412c6fd0e670a 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.
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