Buchwald–Hartwig amination: N-(4-Chloropyridin-2-yl)acetamide → N-[4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-2-pyridinyl]acetamide
83% 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)acetamide | C₇H₇ClN₂O | |
| Reactant | 5-Chloro-1,3-benzodioxol-4-amine | C₇H₆ClNO₂ | |
| 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-[(5-chloro-1,3-benzodioxol-4-yl)amino]-2-pyridinyl]acetamide | C₁₄H₁₂ClN₃O₃ | 83.06% |
Conditions
- Temperature
- 150 °C
Yield
- 83% of N-[4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-2-pyridinyl]acetamide.
Procedure
Copied from the source record, unedited
Reaction carried out in two batches in 20 ml microwave tubes. 5-chlorobenzo[d][1,3]dioxol-4-amine (1 g, 5.83 mmol), N-(4-chloropyridin-2-yl)acetamide (0.994 g, 5.83 mmol), XANTPHOS (0.405 g, 0.70 mmol), PALLADIUM(II) ACETATE (0.065 g, 0.29 mmol) and CESIUM CARBONATE (3.80 g, 11.66 mmol) were suspended in 2x DMA (12mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LC/MS showed completion. The reaction mixture was concentrated and diluted with EtOAc , and washed sequentially with water and saturated brine. The organic layer was dried over MgSO4, filtered and evaporated. The crude oil was triturated with EtOAc, Et2O and hexane to give a solid which was collected by filtration and dried under vacuum to give P1 N-(
The source
This record comes from experimental reaction archive (ord-3e57b5a0d75c4f5d9c22ce74626f60c3). Open the source and check it against what is on this page.
experimental reaction archive record ord-3e57b5a0d75c4f5d9c22ce74626f60c3 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.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.