Buchwald–Hartwig amination, record ord-fde5e0f95519439ca9660af435fc14a6
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Chloro-3-fluoro-5-methylpyridine | C₆H₅ClFN | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Sodium Hydroxide | HNaO | |
| 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.
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 (105 mg, 0.89 mmol) and 2-chloro-3-fluoro-5-methylpyridine (100 mg, 0.69 mmol) in dioxane (10 mL) at 21°C. The resulting mixture was stirred at 100 °C for 2 hours.Cooled. Adsorbed onto silica. The crude product was purified by flash silica chromatography, elution gradient 10 to 30% DCM in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 3-fluoro-5-methylpyridin-2-ylcarbamate (40.0 mg, 25.7 %) as a cream solid. not pure enough to register ..
The source
This record comes from experimental reaction archive (ord-fde5e0f95519439ca9660af435fc14a6). Open the source and check it against what is on this page.
experimental reaction archive record ord-fde5e0f95519439ca9660af435fc14a6 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.