Buchwald–Hartwig amination: 6-Chloronicotinamide → 6-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide
0% yield, run at 120 °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 | 6-Chloronicotinamide | C₆H₅ClN₂O | |
| Reactant | 3-(Trifluoromethyl)benzylamine | C₈H₈F₃N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 6-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide | C₁₄H₁₂F₃N₃O | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of 6-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide.
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
To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.020 g, 0.03 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (3-(trifluoromethyl)phenyl)methanamine (0.049 mL, 0.34 mmol). The reaction was run in microwave at 120 C for 4h. only traces of product observed. Reaction wasted.
The source
This record comes from experimental reaction archive (ord-058876800e774f05bf1b52bd00238231). Open the source and check it against what is on this page.
experimental reaction archive record ord-058876800e774f05bf1b52bd00238231 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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