Buchwald–Hartwig amination: 2,3-Dichloropyridine → N-(3-chloro-2-pyridinyl)benzamide
11% yield, run at 110 °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 | 2,3-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | Benzamide | C₇H₇NO | |
| 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-(3-chloro-2-pyridinyl)benzamide | C₁₂H₉ClN₂O | 10.78% |
Conditions
- Temperature
- 110 °C
Yield
- 11% of N-(3-chloro-2-pyridinyl)benzamide.
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.
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
- N-pyridin-3-ylbenzamidenot recorded
Procedure
Copied from the source record, unedited
In a 5 mL vial were added Pd(OAc)2 (6.85 mg, 0.03 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (35.3 mg, 0.06 mmol), N-(3-chloropyridin-2-yl)benzamide (15.30 mg, 10.78 %) and cesium carbonate (477 mg, 1.46 mmol) in dioxane (2 mL) to give a yellow solution. The flask was evacuated and filled with Nitrogen three times. Then, 2,3-dichloropyridine (99 mg, 0.67 mmol) was added. The reaction mixture was stirred overnight at 80°C. The reaction mixture was diluted with EtOAc (3 mL) and filtered. The solid was washed with EtOAc and the collected organic layers were evaporated to dryness, to give the crude product. The compound was purified by preparative HPLC on a Kromasil C8 column (10 µm 250x20 ID mm) using a gradient of 10-50% acetonitrile in H2O/ACN/FA 95/5/0.2 buffer, ove
The source
This record comes from experimental reaction archive (ord-bb9134ed03e248f6b9498f9cb351f5cb). Open the source and check it against what is on this page.
experimental reaction archive record ord-bb9134ed03e248f6b9498f9cb351f5cb 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
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