Buchwald–Hartwig amination, record ord-805e4c9d19604f5ca8a6f376906a62c5
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 | Ethyl 6-bromo-4-[(2,4-dichlorophenyl)amino]-7-methoxyquinoline-3-carboxylate | C₁₉H₁₅BrCl₂N₂O₃ | |
| Reactant | 1-Methylpiperazine | C₅H₁₂N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 4-[(2,4-dichlorophenyl)amino]-7-methoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate | C₂₄H₂₆Cl₂N₄O₃ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of Ethyl 4-[(2,4-dichlorophenyl)amino]-7-methoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate.
Procedure
Copied from the source record, unedited
To a solution of ethyl 6-bromo-4-(2,4-dichlorophenylamino)-7-methoxyquinoline-3-carboxylate (694 mg, 1.48 mmol) and 1-methylpiperazine (0.246 mL, 2.21 mmol) in dioxane (10 mL) was added cesium carbonate (962 mg, 2.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (67.6 mg, 0.07 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (92 mg, 0.15 mmol). Reaction vessel in oil bath set to 100 °C. 2.15pm o/n 20 hours - LCMS shows product (489) and SM (470) 26 hours - ratio of product : SM looks better by MS. 2 x o/n - small SM peak remaining in MS. Concentrated onto silica and purified on ISCO. 40g column, 4:1 H:EA, then gradient up to ~1:1 EA:MeOH. Can't find product by LCMS in any fractions. NMR of polar fractions may be acid from Buchwald coupling. Need to purify SM on column, rep
The source
This record comes from experimental reaction archive (ord-805e4c9d19604f5ca8a6f376906a62c5). Open the source and check it against what is on this page.
experimental reaction archive record ord-805e4c9d19604f5ca8a6f376906a62c5 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.