Buchwald–Hartwig amination: 2,5-Dichloro-4-iodopyridine → 2-(2,5-dichloropyridin-4-ylamino)-5-fluoro-N-methylbenzamide
13% yield, run at 80 °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 | 2,5-Dichloro-4-iodopyridine | C₅H₂Cl₂IN | |
| Reactant | 2-Amino-5-fluoro-N-methylbenzamide | C₈H₉FN₂O | |
| 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 | 2-(2,5-dichloropyridin-4-ylamino)-5-fluoro-N-methylbenzamide | C₁₃H₁₀Cl₂FN₃O | 13.27% |
Conditions
- Temperature
- 80 °C
Yield
- 13% of 2-(2,5-dichloropyridin-4-ylamino)-5-fluoro-N-methylbenzamide.
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
palladium acetate (31.2 mg, 0.14 mmol) was added to 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (121 mg, 0.21 mmol), Cesium carbonate (2266 mg, 6.95 mmol), 2-amino-5-fluoro-N-methylbenzamide (585 mg, 3.48 mmol) and 2,5-dichloro-4-iodopyridine (1000 mg, 3.65 mmol) in dioxane (20 mL) under nitrogen. The resulting suspension was stirred at 80 °C for 18hrs then cooled. Product appeared to be out of solution. Product and bis product suggested. Disappointing! The reaction mixture was evaporated to dryness and redissolved in EtOAc (100 mL), and washed sequentially with saturated Na2CO3 (50 mL), water (50 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elut
The source
This record comes from experimental reaction archive (ord-2bb50d74d5eb4051be498e22a50f1370). Open the source and check it against what is on this page.
experimental reaction archive record ord-2bb50d74d5eb4051be498e22a50f1370 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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