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
33% yield, run at 130 °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 | 1,8-Diazabicyclo(5.4.0)undec-7-ene | C₉H₁₆N₂ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | N-[4-[(6-Chloro-[1,3]dioxolo[4,5-B]pyridin-7-Yl)amino]-2-Pyridyl]cyclopropanecarboxamide | C₁₅H₁₃ClN₄O₃ | 32.5% |
Conditions
- Temperature
- 130 °C
Yield
- 33% 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% |
| 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% (this run) |
Procedure
Copied from the source record, unedited
2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.190 mL, 1.27 mmol) was added to a mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (100 mg, 0.51 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (105 mg, 0.61 mmol) and BIS(DIBENZYLIDENEACETONE)PALLADIUM(0) (26.3 mg, 0.05 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (29.4 mg, 0.05 mmol) in toluene (1 mL) in a microwave tube. The reaction was degased, purged with argon and heated to 130 °C over a period of 7 hours in an oil bath. The mixture was diluted with dichloromethane, washed with water (emulsion), with brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 3% methanol in dichloromethane. The solvent was evaporated to drynes
The source
This record comes from experimental reaction archive (ord-1aa2de1a9b014f58b717c720b31e4a66). Open the source and check it against what is on this page.
experimental reaction archive record ord-1aa2de1a9b014f58b717c720b31e4a66 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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Where to next
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