Buchwald–Hartwig amination, record ord-e759a68ff56d4b3bb4604b0f87a340c5
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-(4-Bromo-phenyl)-1-[5-methoxy-8-(4-methyl-piperazin-1-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-ethanone | C₂₃H₂₈BrN₃O₂ | |
| Reactant | Piperidine | C₅H₁₁N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 1-[5-Methoxy-8-(4-methyl-piperazin-1-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-(4-piperidin-1-yl-phenyl)-ethanone | C₂₈H₃₈N₄O₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 1-[5-Methoxy-8-(4-methyl-piperazin-1-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-2-(4-piperidin-1-yl-phenyl)-ethanone.
Procedure
Copied from the source record, unedited
2-(4-bromophenyl)-1-(5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (125 mg, 0.27 mmol),[Reactants],piperidine (23.22 mg, 0.27 mmol) was taken in a mixture of DME (5 mL):water (1.250 mL) under N2.The reaction mixture was purged under N2 for 10 min.Tris(dibenzylideneacetone)dipalladium (0) (14.98 mg, 0.02 mmol) was added to the above reaction.The resulting reaction was stirred for 3 hrs at reflux tempt.LCMS profile showed formation of required product.Reaction was cooled to rt,solvents was evapourated to dryness.Crude was diluted with DCM and water (min) and organic layer separated and concentrated .Purification was done on RP systme to get product 1-(5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-(piperidin-1-yl)phenyl)ethanone as
The source
This record comes from experimental reaction archive (ord-e759a68ff56d4b3bb4604b0f87a340c5). Open the source and check it against what is on this page.
experimental reaction archive record ord-e759a68ff56d4b3bb4604b0f87a340c5 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.