Buchwald–Hartwig amination: ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate → 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester
48% 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 | ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate | C₁₃H₁₁BrO₅ | |
| Reactant | 1-Benzylpiperazine | C₁₁H₁₆N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester | C₂₄H₂₆N₂O₅ | 48.39% |
Conditions
- Temperature
- 80 °C
Yield
- 48% of 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester.
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
Tris(dibenzylideneacetone)dipalladium(0) (0.280 g, 0.31 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.457 g, 0.73 mmol), ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate (2 g, 6.11 mmol), 1-benzylpiperazine (1.169 mL, 6.73 mmol) and cesium carbonate (2.79 g, 8.56 mmol) were heated under argon to 80 °C in toluene (60 mL) overnight. The reaction mixture was allowed to cool. Ethylacetate was added and the organic mixture was filtered. The filtrate was evaporated onto Silica gel. The crude product was added to a silica gel column and was eluted with MeOH/DCM 0-5%. 1H NMR in CDCl3 is consistent with desired product MS (m+1) = 423. HPLC Peak RT = 3.38 minutes is product. Purity = 63%.
The source
This record comes from experimental reaction archive (ord-a7f71cce88db46cba0388c01927b5a88). Open the source and check it against what is on this page.
experimental reaction archive record ord-a7f71cce88db46cba0388c01927b5a88 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
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