Buchwald–Hartwig amination: 2-(2-Chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide → 2-[[5-cyano-2-[(3-methoxy-1-methylpyrazol-5-yl)amino]-4-pyridinyl]amino]-N-methylbenzamide
55% yield, run at 90 °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 | 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.
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
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.
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