Buchwald–Hartwig amination: 3-Bromopyridine → tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate
0% yield, run at 85 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromopyridine | C₅H₄BrN | |
| Reactant | (R)-1-Boc-3-methylpiperazine | C₁₀H₂₀N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate | C₁₅H₂₃N₃O₂ | 0% |
Conditions
- Temperature
- 85 °C
Yield
- 0% of tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Palladium (II) acetate | sodium 2-methylpropan-2-olate | Toluene | 100 °C | — | 103% |
| 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl; Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 0% |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Bis(dibenzylideneacetone)palladium | sodium 2-methylpropan-2-olate | Toluene | 85 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.145 g, 0.16 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.183 g, 0.32 mmol) were added to a mixture of Sodium tert-butoxide (0.912 g, 9.49 mmol), 3-bromopyridine (0.610 mL, 6.33 mmol),(R)-tert-butyl 3-methylpiperazine-1-carboxylate (1.901 g, 9.49 mmol) and toluene (20 mL) under nitrogen. The mixture was heated at 85 °C for 16 hours before being cooled to RT and filtered through celite. The filtrate was concentrated and the reaction mixture was seperated by flash silica chromatography, elution gradient 20 to 40% EtOAc in heptane. No product was isolated. .
The source
This record comes from experimental reaction archive (ord-d7d7e0dc4c0741f08ecfdb907acad13f). Open the source and check it against what is on this page.
experimental reaction archive record ord-d7d7e0dc4c0741f08ecfdb907acad13f 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
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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