Buchwald–Hartwig amination: N-(4-chloropyridin-2-yl)cyclopropanecarboxamide → N-[4-(1,3-benzodioxol-4-ylamino)-2-pyridinyl]cyclopropanecarboxamide
51% yield, run at 150 °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 | N-(4-chloropyridin-2-yl)cyclopropanecarboxamide | C₉H₉ClN₂O | |
| Reactant | 1,3-Benzodioxol-4-amine | C₇H₇NO₂ | |
| 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 | Dimethylacetamide | C₄H₉NO | |
| Product | N-[4-(1,3-benzodioxol-4-ylamino)-2-pyridinyl]cyclopropanecarboxamide | C₁₆H₁₅N₃O₃ | 50.74% |
Conditions
- Temperature
- 150 °C
Yield
- 51% of N-[4-(1,3-benzodioxol-4-ylamino)-2-pyridinyl]cyclopropanecarboxamide.
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
benzo[d][1,3]dioxol-4-amine (100 mg, 0.73 mmol), N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (143 mg, 0.73 mmol), XANTPHOS (50.6 mg, 0.09 mmol), PALLADIUM(II) ACETATE (8.19 mg, 0.04 mmol) and CESIUM CARBONATE (475 mg, 1.46 mmol) were suspended in DMA (3mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 1.5 hours in the microwave reactor and cooled to RT. LC/MS showed completion. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 0.35M NH3/MeOH and pure fractions were evaporated to dryness to afford N-(4-(benzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)cyclopropanecarboxamide as a brown oil. The crude product was purified by preparative HPLC using decreasingly polar mixtures of wa
The source
This record comes from experimental reaction archive (ord-0781cd6f039348aeb189dfde52dad6f2). Open the source and check it against what is on this page.
experimental reaction archive record ord-0781cd6f039348aeb189dfde52dad6f2 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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