Buchwald–Hartwig amination: 6-chloro-2H-[1,3]dioxolo[4,5-b]pyridin-7-amine → N-[4-[(6-Chloro-[1,3]dioxolo[4,5-B]pyridin-7-Yl)amino]-2-Pyridyl]cyclopropanecarboxamide
71% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 6-chloro-2H-[1,3]dioxolo[4,5-b]pyridin-7-amine | C₆H₅ClN₂O₂ | |
| Reactant | N-(4-chloropyridin-2-yl)cyclopropanecarboxamide | C₉H₉ClN₂O | |
| 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 | N-[4-[(6-Chloro-[1,3]dioxolo[4,5-B]pyridin-7-Yl)amino]-2-Pyridyl]cyclopropanecarboxamide | C₁₅H₁₃ClN₄O₃ | 70.91% |
Conditions
- Temperature
- 100 °C
Yield
- 71% of N-[4-[(6-Chloro-[1,3]dioxolo[4,5-B]pyridin-7-Yl)amino]-2-Pyridyl]cyclopropanecarboxamide.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 71% (this run) |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | 1,8-Diazabicyclo(5.4.0)undec-7-ene | Toluene | 130 °C | — | 33% |
Procedure
Copied from the source record, unedited
A mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (1 g, 5.09 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.878 g, 5.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.324 g, 0.56 mmol), diacetoxypalladium (0.090 g, 0.40 mmol), cesium carbonate (4.14 g, 12.71 mmol) and dioxane (18 mL) was degased, purged (x3) with argon and heated to reflux over a period of 4 hours in an oil bath (110°C). The reaction was complete. The reaction mixture was allowed to warm to room temperature diluted with water (25ml), a saturated solution of NH4Cl (35ml). Extraction with dichloromethane (x2), the organic was washed with a saturated aqueous solution of brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica
The source
This record comes from experimental reaction archive (ord-97d4ec8781d24990b921a4f59e0aac9e). Open the source and check it against what is on this page.
experimental reaction archive record ord-97d4ec8781d24990b921a4f59e0aac9e 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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