Buchwald–Hartwig amination, record ord-fbf696d6dcb34e7c9c731cbe586b831a
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 | Methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | C₁₄H₁₈BClO₄ | |
| Reactant | Aniline | C₆H₇N | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | C₁₂H₂₇P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | C₂₀H₂₄BNO₄ | 2.29% |
Conditions
- Temperature
- 100 °C
Yield
- 2% of Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate.
Procedure
Copied from the source record, unedited
aniline (0.162 mL, 1.78 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (440mg, 1.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (13.59 mg, 0.01 mmol), tri- tert-butylphosphine (10.80 µL, 0.04 mmol) and potassium phosphate (441 mg, 2.08 mmol) in degassed DME (6 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 2 days. The reaction mixture was diluted with Et2O (50 mL), and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, elution 10 to 60% EtOAc in heptane.
The source
This record comes from experimental reaction archive (ord-fbf696d6dcb34e7c9c731cbe586b831a). Open the source and check it against what is on this page.
experimental reaction archive record ord-fbf696d6dcb34e7c9c731cbe586b831a 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.