Buchwald–Hartwig amination: 3,5-Dibromopyridine → 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine
12% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 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 | 3,5-Dibromopyridine | C₅H₃Br₂N | |
| Reactant | 4-Fluoro-N-methylaniline | C₇H₈FN | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | C₂₄H₃₁P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine | C₁₂H₁₀BrFN₂ | 12.46% |
Conditions
- Temperature
- 110 °C
Yield
- 12% of 5-bromo-N-(4-fluorophenyl)-N-methylpyridin-3-amine.
Every recorded run making this product
2 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)biphenyl; Bis(dibenzylideneacetone)palladium | potassium 2-methylpropan-2-olate | Toluene | 110 °C | — | 12% (this run) |
| 2-(Dicyclohexylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Toluene | 110 °C | — | 0% |
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask (t=g) was 4-fluoro-N-methylaniline (1 g, 7.99 mmol), 3,5-dibromopyridine (2.272 g, 9.59 mmol), and Pd2(dba)3 (0.366 g, 0.40 mmol) in toluene (16 mL) ([VOLUME]) to give a purple suspension. biphenyl-2-yldicyclohexylphosphine (0.420 g, 1.20 mmol) and KOtBu (1.166 g, 10.39 mmol) were added. Reaction was allowed to stir for 1.5 hours at which point LC/MS was taken which indicated that all the dibromopyridine had been consumed. Reaction was quenched by addition of excess ammonium chloride. Mixture was filtered though a plug of celite, extracted with ethyl acetate. The organic fractions were collected and washed with water, then dried over NaSO4, rotovapped down to an oil, redissolved in DCM then purified over a 120g column using 5 minutes of pure hexane, follow
The source
This record comes from experimental reaction archive (ord-49953a76cfae45059ad30fb1a9e6e7be). Open the source and check it against what is on this page.
experimental reaction archive record ord-49953a76cfae45059ad30fb1a9e6e7be 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.
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More Buchwald–Hartwig amination records
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