Buchwald–Hartwig amination: Methyl 4-iodosalicylate → Tert-butyl 4-(3-hydroxy-4-methoxycarbonylphenyl)piperazine-1-carboxylate
0% yield, run at 90 °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 4-iodosalicylate | C₈H₇IO₃ | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | Tert-butyl 4-(3-hydroxy-4-methoxycarbonylphenyl)piperazine-1-carboxylate | C₁₇H₂₄N₂O₅ | 0% |
Conditions
- Temperature
- 90 °C
Yield
- 0% of Tert-butyl 4-(3-hydroxy-4-methoxycarbonylphenyl)piperazine-1-carboxylate.
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.
- Methyl 4-(4-Boc-1-piperazinyl)-2-chlorobenzoate91%
- Tert-butyl 4-(7-benzo[b]furanyl)piperazine-1-carboxylate84%
- Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate83%
- Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate82%
- Tert-butyl 4-(5-(benzyloxy)pyridin-2-YL)piperazine-1-carboxylate69%
- tert-Butyl 4-(2-(ethoxycarbonyl)benzofuran-4-yl)piperazine-1-carboxylate64%
- Tert-butyl 4-(2-methoxyphenyl)piperazine-1-carboxylate62%
- tert-butyl 4-(2-methyl-3-oxo-1H-isoindol-5-yl)piperazine-1-carboxylate57%
- Tert-butyl 4-(4-acetylphenyl)piperazine-1-carboxylate52%
- Tert-butyl 4-(3-chloro-4-cyanophenyl)piperazine-1-carboxylate47%
- tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate46%
- Tert-butyl 4-[6-[(4-methylsulfonylphenyl)methoxy]-3-pyridinyl]piperazine-1-carboxylate43%
Procedure
Copied from the source record, unedited
tert-butyl piperazine-1-carboxylate (0.670 g, 3.60 mmol) and methyl 2-hydroxy-4-iodobenzoate (1 g, 3.60 mmol), BINAP (0.224 g, 0.36 mmol), cesium carbonate (2.461 g, 7.55 mmol) were put inDME (18 mL), tris(dibenzylideneacetone)dipalladium(0) (0.165 g, 0.18 mmol) was added last. Reaction wsa purged by nitrogen, and heated at90 °C overnight. No desired product was found.
The source
This record comes from experimental reaction archive (ord-50654e3db36e4cb59399fcb1f475b246). Open the source and check it against what is on this page.
experimental reaction archive record ord-50654e3db36e4cb59399fcb1f475b246 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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