Buchwald–Hartwig amination: Ethyl 5-bromopyridine-3-carboxylate → Ethyl 5-morpholin-4-ylpyridine-3-carboxylate
0% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Ethyl 5-bromopyridine-3-carboxylate | C₈H₈BrNO₂ | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | C₂₆H₃₆NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 5-morpholin-4-ylpyridine-3-carboxylate | C₁₂H₁₆N₂O₃ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of Ethyl 5-morpholin-4-ylpyridine-3-carboxylate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- Dimethyl 5-morpholinoisophthalate78%
- Ethyl 4-(2-fluoro-4-methylanilino)-7-(2-methoxyethoxy)-6-morpholin-4-ylquinoline-3-carboxylate75%
- N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide64%
- 4-(6-Bromopyridin-3-yl)morpholine56%
- 4-(5-Bromopyridin-3-yl)morpholine50%
- Methyl 3-bromo-4-morpholinobenzoate32%
- 4-Morpholinophenol31%
- 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide30%
- 5-Morpholin-4-yl-nicotinic acid tert-butyl ester27%
- (5-Morpholinopyridin-2-yl)methanol19%
- 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(3-morpholin-4-ylphenyl)methyl]benzamide18%
- Methyl 5-bromo-2-morpholinobenzoate18%
Procedure
Copied from the source record, unedited
ethyl 5-bromonicotinate (200 mg, 0.87 mmol), morpholine (0.083 mL, 0.96 mmol), sodium 2-methylpropan-2-olate (167 mg, 1.74 mmol), 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (17.11 mg, 0.04 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (19.90 mg, 0.02 mmol) were suspended in dioxane (5 mL) and sealed into a microwave tube. The reaction was heated to 100 °C for 1 hour in the microwave reactor and cooled to RT. LCMS analysis appeared to indicate addition of 2 morpholine rings and the reaction was abandoned.
The source
This record comes from experimental reaction archive (ord-2f71fc02b38b41c2a59bfdd4b865c8b3). Open the source and check it against what is on this page.
experimental reaction archive record ord-2f71fc02b38b41c2a59bfdd4b865c8b3 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.
Where to next
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