Buchwald–Hartwig amination: 3,5-Dibromopyridine → 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine
51% 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 | (R)-3-Methoxypyrrolidine | C₅H₁₁NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine | C₁₀H₁₃BrN₂O | 51.14% |
Conditions
- Temperature
- 90 °C
Yield
- 51% of 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine.
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 (0.644 g, 2.72 mmol), (R)-3-methoxypyrrolidine (0.25 g, 2.47 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.045 g, 0.05 mmol), sodium 2-methylpropan-2-olate (0.356 g, 3.71 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.077 g, 0.12 mmol) in degassed toluene (7.5 ml) was sealed into a microwave tube and stirred for 16 hours at 90 °C. The reaction was completed. After cooling, an aqueous solution of Na2CO3 was added. Extraction with DCM (twice). The organic layers were dried over MgSO4 and evaporated _in vacuo_ to give the crude product as an orange oil. PBO-04062-54-01 It was purified by chromatography (Merck cartridge SVF D26 - SI60 15-40 µm - 30 g) on silica gel eluting with EtOAc 0 to 25% in petroleum ether. Pure collected fractions were ev
The source
This record comes from experimental reaction archive (ord-29d169023edf45ffb5746904d99b3825). Open the source and check it against what is on this page.
experimental reaction archive record ord-29d169023edf45ffb5746904d99b3825 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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