Buchwald–Hartwig amination, record ord-ff15f562a6534424848273f847da5684
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 | N-(1,3-dimethylpyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine | C₁₁H₁₀F₃IN₄ | |
| Reactant | 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one | C₁₀H₁₂N₂O | |
| 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 | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 8-[[2-[(1,3-Dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one | C₂₁H₂₁F₃N₆O | 33.74% |
Conditions
- Temperature
- 80 °C
Yield
- 34% of 8-[[2-[(1,3-Dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one.
Procedure
Copied from the source record, unedited
A suspension of 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (23.06 mg, 0.13 mmol), N-(1,3-dimethyl-1H-pyrazol-4-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (7.57 mg, 0.01 mmol) and cesium carbonate (85 mg, 0.26 mmol) was stirred at 80 °C overnight under nitrogen. LCMS showed formation of more bis-arylation by-product than in _EN01775-08_ (DMA under micorwaves conditions). The crude was combined with EN01775-08-01 and poured onto a silicagel column. The crude product was purified by flash chromatography eluting with 0 to 5% methanol in ethyl acetate/DCM (1/1). The solvent was evaporated to dryness to afford a gummy film in the flask **(37mg: not that bad)**. it was
The source
This record comes from experimental reaction archive (ord-ff15f562a6534424848273f847da5684). Open the source and check it against what is on this page.
experimental reaction archive record ord-ff15f562a6534424848273f847da5684 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.