Buchwald–Hartwig amination: 2,6-Dichloroisonicotinic acid → 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid
0% yield, run at 100 °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 | 2,6-Dichloroisonicotinic acid | C₆H₃Cl₂NO₂ | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid | C₁₁H₁₃ClN₂O₄ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid.
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.
- tert-butyl N-(5-chloropyridazin-3-yl)carbamate100%
- tert-butyl N-(3-fluoro-4-formylphenyl)carbamate97%
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester0%
- (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester0%
- tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate0%
- 3-(Boc-amino)pyridinenot recorded
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
Procedure
Copied from the source record, unedited
Reagents were mixed in a 25 mL round bottom flask and flushed well with nitrogen - heated at 100 °C for 16 h. The mixture looked dark black. Could not detect any starting material or product! It was discarded.
The source
This record comes from experimental reaction archive (ord-7c9ead47a3324fac997f2b8af6afca02). Open the source and check it against what is on this page.
experimental reaction archive record ord-7c9ead47a3324fac997f2b8af6afca02 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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