Buchwald–Hartwig amination: 3,5-Dibromopyridine → 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone
32% yield, run at 140 °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 | 1-Acetylpiperazine | C₆H₁₂N₂O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Product | 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone | C₁₁H₁₄BrN₃O | 31.78% |
Conditions
- Temperature
- 140 °C
Yield
- 32% of 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone.
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.
- 1-[4-(2-Methyl-3-nitrophenyl)piperazin-1-yl]ethanone98%
- 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine68%
- 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine51%
- 4-(5-Bromopyridin-3-yl)morpholine50%
- 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone30%
- 1-(5-Bromopyridin-3-yl)-4-methylpiperazine21%
- 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine12%
- 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine0%
Procedure
Copied from the source record, unedited
3,5-dibromopyridine (1.233 g, 5.20 mmol), 1-(piperazin-1-yl)ethanone (0.734 g, 5.73 mmol), PdOAc2 (0.117 g, 0.52 mmol), XANTPHOS (0.361 g, 0.62 mmol), Cs2CO3 (5.09 g, 15.61 mmol), 1,4-dioxane as added to a 10 mL microwave vial. This was degassed and refilled with N2 and then heated at 140 °C in microwave for 1h. LCMS showed reaction done with the peak at Rf1.24 showed a fragment mass of 284. Evaporated solvent. Residue purified by ISCO (0-20% MeOH in EtOAc )to get the desired product 1-(4-(5-bromopyridin-3-yl)piperazin-1-yl)ethanone (0.470 g, 31.8 %). Trial # 1: 3,5-dibromopyridine (407 mg, 1.72 mmol), 1-(piperazin-1-yl)ethanone (231 mg, 1.81 mmol), PdOAc2 (38.6 mg, 0.17 mmol), XANTPHOS (119 mg, 0.21 mmol), Cs2CO3 (1681 mg, 5.16 mmol), 1,4-dioxane as added to a 10 mL microwave vial. Th
The source
This record comes from experimental reaction archive (ord-b3c4a680709749268aeba07b670223ef). Open the source and check it against what is on this page.
experimental reaction archive record ord-b3c4a680709749268aeba07b670223ef 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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