Buchwald–Hartwig amination: 3,5-Dibromopyridine → 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine
68% yield, run at 90 °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 | 3,5-Dibromopyridine | C₅H₃Br₂N | |
| Reactant | (2-Methoxyethyl)(methyl)amine | C₄H₁₁NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine | C₉H₁₃BrN₂O | 67.64% |
Conditions
- Temperature
- 90 °C
Yield
- 68% of 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine.
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.
Procedure
Copied from the source record, unedited
A mixture of 3,5-dibromopyridine (1.468 mL, 6.17 mmol), 2-methoxy-N- methylethanamine (0.602 mL, 5.61 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.103 g, 0.11 mmol), sodium 2-methylpropan-2-olate (0.809 g, 8.41 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.175 g, 0.28 mmol) in degassed toluene (15 mL) was stirred for 16 hours at 90 °C in a sealed vessel under inert atmosphere. LC MS of the crude mixture: FLA 04227-53-01. Extraction with sat. aq. Na2CO3 solution and AE, then back extraction 2x NaCl sat using DCM. The organics were dried over MgSO4 and evaporated _in vacuo_. The residue was purified by chromatography (11 cm SiO2, diameter: 3.5 cm) eluent: AE/hex 25/75to 40/60 to provide 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine (0.930 g, 67.6 %) as a yellow oil. 1H NM
The source
This record comes from experimental reaction archive (ord-3d99515de30641289be85a9d48e7a43a). Open the source and check it against what is on this page.
experimental reaction archive record ord-3d99515de30641289be85a9d48e7a43a 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.
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Where to next
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