Buchwald–Hartwig amination, record ord-b3b59923db4e4673a6bcde3d5a9c7727
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 | CCOC(=O)c1cnc2cc(OCCOC)c(Br)cc2c1Nc1ccc(C)cc1F | C₂₂H₂₂BrFN₂O₄ | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 4-(2-fluoro-4-methylanilino)-7-(2-methoxyethoxy)-6-morpholin-4-ylquinoline-3-carboxylate | C₂₆H₃₀FN₃O₅ | 74.65% |
Conditions
- Temperature
- 80 °C
Yield
- 75% of Ethyl 4-(2-fluoro-4-methylanilino)-7-(2-methoxyethoxy)-6-morpholin-4-ylquinoline-3-carboxylate.
Procedure
Copied from the source record, unedited
Reaction reference EN00057-06, EN02095-49, 67, 68, 74, 78, 90 In a 50 mL round-bottomed flask was ethyl 6-bromo-4-(2-fluoro-4-methylphenylamino)-7-(2-methoxyethoxy)quinoline-3-carboxylate (4.6911 g, 9.83 mmol), Morpholine (0.857 mL, 9.83 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.720 g, 0.79 mmol), and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (1.958 g, 3.14 mmol) in Dioxane (100 mL) to give a orange suspension. The reaction mixture was heated and stirred at 80°C (start 4pm). After stirring/heating overngiht, reaction is about 30% complete. Add rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (1.958 g, 3.14 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.720 g, 0.79 mmol). Continue heating/stirring. After heating and stirring for another 24hr, reaction is about 85% com
The source
This record comes from experimental reaction archive (ord-b3b59923db4e4673a6bcde3d5a9c7727). Open the source and check it against what is on this page.
experimental reaction archive record ord-b3b59923db4e4673a6bcde3d5a9c7727 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.