Buchwald–Hartwig amination: Methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → Methyl 3-anilino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
0% yield, run at 100 °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 | 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 | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% 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 (0.360 mL, 3.95 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (900 mg, 3.03 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (139 mg, 0.15 mmol), [Reactants] and potassium phosphate (1546 mg, 7.28 mmol) in degassed DME (10 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 24 hours. The reaction mixture was allowed to cool then filtered through celite, washing with ethyl acetate. The filtrate was evaporated under reduced pressure to give a brown residue. Not progressed any further.
The source
This record comes from experimental reaction archive (ord-7f4bd58c1e854ed5b839b01e20dd39d2). Open the source and check it against what is on this page.
experimental reaction archive record ord-7f4bd58c1e854ed5b839b01e20dd39d2 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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