Buchwald–Hartwig amination, record ord-2e4132c3c32149d3a68cd64301eacce5
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-Chloro-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile | C₁₆H₁₃ClN₄O | |
| Reactant | 1,3-dimethyl-1H-pyrazol-4-amine | C₅H₉N₃ | |
| 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 | 6-[(1,3-Dimethylpyrazol-4-yl)amino]-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile | C₂₁H₂₁N₇O | 7.33% |
Conditions
- Temperature
- 90 °C
Yield
- 7% of 6-[(1,3-Dimethylpyrazol-4-yl)amino]-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile.
Procedure
Copied from the source record, unedited
6-chloro-4-(2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-8-ylamino)nicotinonitrile (595 mg, 1.90 mmol), Palladium(II) acetate (34.2 mg, 0.15 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (132 mg, 0.23 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (423 mg, 3.80 mmol) and Cesium carbonate (744 mg, 2.28 mmol) were suspended in dioxane (40 mL). The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 2 hour with stirring. The reaction was cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product .The crude product was purified by preparative basic HPLC. Fractions containing the desired compound we
The source
This record comes from experimental reaction archive (ord-2e4132c3c32149d3a68cd64301eacce5). Open the source and check it against what is on this page.
experimental reaction archive record ord-2e4132c3c32149d3a68cd64301eacce5 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.