Buchwald–Hartwig amination, record ord-d012fdccb17647d4838efd4e1491311e
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 | 2-(2-Chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide | C₁₄H₁₁ClN₄O | |
| Reactant | 3-methoxy-1-methyl-1H-pyrazol-5-amine | C₅H₉N₃O | |
| 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 | 2-[[5-cyano-2-[(3-methoxy-1-methylpyrazol-5-yl)amino]-4-pyridinyl]amino]-N-methylbenzamide | C₁₉H₁₉N₇O₂ | 54.7% |
Conditions
- Temperature
- 90 °C
Yield
- 55% of 2-[[5-cyano-2-[(3-methoxy-1-methylpyrazol-5-yl)amino]-4-pyridinyl]amino]-N-methylbenzamide.
Procedure
Copied from the source record, unedited
2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (100 mg, 0.35 mmol), Palladium(II) acetate (6.26 mg, 0.03 mmol), [Reactants], 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (24.22 mg, 0.04 mmol) and Cesium carbonate (136 mg, 0.42 mmol) were suspended in dioxane (3 mL) into a test tube. The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 18 hours with stirring. The reaction was cooled to 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 HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using de
The source
This record comes from experimental reaction archive (ord-d012fdccb17647d4838efd4e1491311e). Open the source and check it against what is on this page.
experimental reaction archive record ord-d012fdccb17647d4838efd4e1491311e 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.