Buchwald–Hartwig amination: 2-Chloro-4-methoxypyridine → 4-[(4-Methoxy-2-pyridinyl)amino]benzenesulfonamide
0% yield, run at 150 °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-Chloro-4-methoxypyridine | C₆H₆ClNO | |
| Reactant | Sulfanilamide | C₆H₈N₂O₂S | |
| 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 | N-methyl-2-pyrrolidone | C₅H₉NO | |
| Product | 4-[(4-Methoxy-2-pyridinyl)amino]benzenesulfonamide | C₁₂H₁₃N₃O₃S | 0% |
Conditions
- Temperature
- 150 °C
Yield
- 0% of 4-[(4-Methoxy-2-pyridinyl)amino]benzenesulfonamide.
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.
Procedure
Copied from the source record, unedited
A mixture of 4-aminobenzenesulfonamide (190mg, 1.10 mmol), 2-chloro-4-methoxypyridine (135 mg, 0.94 mmol), diacetoxypalladium (13mg, 0.06 mmol), cesium carbonate (417mg, 1.28 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (50 mg, 0.09 mmol) in NMP (2.0 mL) was heated **in the microwave** for 10 min at 150 °C. LC MS crude mix. FLA-04227-80-01 showed no reaction. Another 30 min at 150°C in the microwave provided FLA-04227-80-02 (crude mix.). No product. **Discard.**
The source
This record comes from experimental reaction archive (ord-370d0a5fbe29487785ea2b57f66774a2). Open the source and check it against what is on this page.
experimental reaction archive record ord-370d0a5fbe29487785ea2b57f66774a2 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
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