Buchwald–Hartwig amination, record ord-70ea34f4ab314aa093c5c77488bf98e8
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 | 2-Chloroquinoline | C₉H₆ClN | |
| Reactant | tert-Butyl piperazine-1-carboxylate | C₉H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate | C₁₈H₂₃N₃O₂ | 46.36% |
Conditions
- Temperature
- 100 °C
Yield
- 46% of tert-Butyl 4-(quinolin-2-yl)piperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
A 2.0-5.0 mL microwave vial was charged with tert-Butyl 1-piperazinecarboxylate (100 mg, 0.54 mmol), 2-Chloroquinoline (0.086 mL, 0.64 mmol), Sodium tert-butoxide (61.9 mg, 0.64 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (33.4 mg, 0.05 mmol) and toluene (3 mL). The reaction mixture was degassed for 10 minutes with nitrogen, and then Tris(dibenzylideneacetone)dipalladium(0) (24.58 mg, 0.03 mmol) was added. The reaction mixture was stirred at 100°C in an oil bath for 12h. The solution was diluted with EtOAc and washed with saturated NaHCO3, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was loaded on a 40g silica gel column and purified on a Teledyne Isco instrument, eluting with 10% to 40% ethyl acetate in heptane. Product
The source
This record comes from experimental reaction archive (ord-70ea34f4ab314aa093c5c77488bf98e8). Open the source and check it against what is on this page.
experimental reaction archive record ord-70ea34f4ab314aa093c5c77488bf98e8 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.