Buchwald–Hartwig amination, record ord-6a2eab081b6a474896fa34b3a81f3801
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 | Methyl 2-amino-2-methylpropanoate | C₅H₁₁NO₂ | |
| Reagent | Sodium 2-methylbutan-2-olate | C₅H₁₁NaO | |
| Catalyst | Bis(adamantan-1-yl)(butyl)phosphane | C₂₄H₃₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | (Trifluoromethyl)benzene | C₇H₅F₃ | |
| Product | Methyl 2-(4-methoxyanilino)-2-methylpropanoate | C₁₂H₁₇NO₃ | 0% |
Conditions
- Temperature
- 180 °C
Yield
- 0% of Methyl 2-(4-methoxyanilino)-2-methylpropanoate.
Procedure
Copied from the source record, unedited
1-bromo-4-methoxybenzene (0.060 mL, 0.47 mmol), methyl 2-amino-2-methylpropanoate (0.05 g, 0.43 mmol), sodium 2-methylbutan-2-olate (0.052 g, 0.47 mmol), diacetoxypalladium (2.68 mg, 0.01 mmol) and methyl 2-(4-methoxyphenylamino)-2-methylpropanoate (0.00 µg) was added to a microwave vial. (TRIFLUOROMETHYL)-BENZENE (0.5 mL) was used as solvent (1-1.2 mL/mmol amine). The mixture was heated in microwave at 180° for 60min. No conversion of startingmaterial was observed.
The source
This record comes from experimental reaction archive (ord-6a2eab081b6a474896fa34b3a81f3801). Open the source and check it against what is on this page.
experimental reaction archive record ord-6a2eab081b6a474896fa34b3a81f3801 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.