Buchwald–Hartwig amination, record ord-14a2a1784ff04475ad4db1893eca50ce
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 | Benzene, 1-bromo-3-nitro- | C₆H₄BrNO₂ | |
| Reactant | 4-(N-Boc-amino)piperidine | C₁₀H₂₀N₂O₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl N-[1-(3-nitrophenyl)piperidin-4-yl]carbamate | C₁₆H₂₃N₃O₄ | 56.63% |
Conditions
- Temperature
- 95 °C
Yield
- 57% of tert-butyl N-[1-(3-nitrophenyl)piperidin-4-yl]carbamate.
Procedure
Copied from the source record, unedited
A 100 mL round bottom flask was charged with a magnetic stir bar, 1-bromo-3-nitrobenzene (1.000 g, 4.95 mmol), [Reactants], Pd2dba3 (0.227 g, 0.25 mmol), BINAP (0.308 g, 0.50 mmol), Cs2CO3 (4.03 g, 12.38 mmol), and toluene (19.80 ml). The vessel was capped with a septum, placed under an atmosphere of argon, and placed in an oil bath heated to 95 °C. The reaction was allowed to stir at this temperature for 16 h before being allowed to cool to rt. The reaction mixture was poured into a separatory funnel containing water (~100 mL) and extracted with ethyl acetate ( 2 x 100 mL). The combined organic extract was dried with MgSO4, filtered, and conc. _in vacuo_ to yield the crude product which was purified via silica gel chromatography (80 g) using ethyl acetate/hexanes (1:5) as eluent to provid
The source
This record comes from experimental reaction archive (ord-14a2a1784ff04475ad4db1893eca50ce). Open the source and check it against what is on this page.
experimental reaction archive record ord-14a2a1784ff04475ad4db1893eca50ce 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.