Buchwald–Hartwig amination, record ord-c7ac817750064edba47d3c6c786a7b69
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 | 6-Chloronicotinamide | C₆H₅ClN₂O | |
| Reactant | 2-(Trifluoromethyl)benzylamine | C₈H₈F₃N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,2-Dimethoxyethane | C₄H₁₀O₂ | |
| Product | 6-[[2-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide | C₁₄H₁₂F₃N₃O | 1.45% |
Conditions
- Temperature
- 120 °C
Yield
- 1% of 6-[[2-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide.
Procedure
Copied from the source record, unedited
To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.021 g, 0.03 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (2-(trifluoromethyl)phenyl)methanamine (0.095 mL, 0.68 mmol). The reaction mixture was subjected to microwave irradiation for 4h at 120 C. Only traces of product was observed. The crude product was dissolved in DMSO (2 mL) and purified using Fractionlynx I, (Xbridge Prep C18 5µm OBD 19x150 mm column), with 5 to 95% acetonitrile in 0.2% ammonia at pH 10. 6-(2-(trifluoromethyl)benzylamino)nicotinamide: 1.45 mg (1.5 %)
The source
This record comes from experimental reaction archive (ord-c7ac817750064edba47d3c6c786a7b69). Open the source and check it against what is on this page.
experimental reaction archive record ord-c7ac817750064edba47d3c6c786a7b69 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.