Buchwald–Hartwig amination: 2-Chloro-3-fluoro-5-methylpyridine → tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate
26% yield, run at 100 °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 | 2-Chloro-3-fluoro-5-methylpyridine | C₆H₅ClFN | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| 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 | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate | C₁₁H₁₅FN₂O₂ | 25.74% |
Conditions
- Temperature
- 100 °C
Yield
- 26% of tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate.
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 |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 26% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Sodium Hydroxide | 1,4-Dioxane | 100 °C | — | 26% |
Procedure
Copied from the source record, unedited
diacetoxypalladium (15.42 mg, 0.07 mmol) and(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (39.8 mg, 0.07 mmol) were added to a degassed mixture of 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol), tert-butyl carbamate (121 mg, 1.03 mmol) and cesium carbonate (336 mg, 1.03 mmol) in dioxane (10 mL) at 21°C. The resulting mixture was stirred at 100 °C for 16 hours.Filtered through celite and adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% DCM in heptane. Pure fractions were evaporated to dryness to afford sm by HNMR Abandoned. ..
The source
This record comes from experimental reaction archive (ord-e2551fd8964c4f0a80ff232c25d61d8a). Open the source and check it against what is on this page.
experimental reaction archive record ord-e2551fd8964c4f0a80ff232c25d61d8a 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
Other runs of this class, one page per distinct transformation.
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