Buchwald–Hartwig amination: 1-Bromo-4-(methylsulphonyl)benzene → 6-chloro-N-(4-methylsulfonylphenyl)pyrazin-2-amine
70% yield, run at 85 °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 | 1-Bromo-4-(methylsulphonyl)benzene | C₇H₇BrO₂S | |
| Reactant | 2-Amino-6-Chloropyrazine | C₄H₄ClN₃ | |
| 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 | 6-chloro-N-(4-methylsulfonylphenyl)pyrazin-2-amine | C₁₁H₁₀ClN₃O₂S | 70.39% |
Conditions
- Temperature
- 85 °C
Yield
- 70% of 6-chloro-N-(4-methylsulfonylphenyl)pyrazin-2-amine.
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
1-bromo-4-(methylsulfonyl)benzene (18.6 g, 79.12 mmol) then cesium carbonate (33.5 g, 102.85 mmol) were successively added to a solution of 6-chloropyrazin-2-amine (10.25 g, 79.12 mmol) in 1,4-dioxane (300 ml). The mixture was purged with nitrogen, then (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.75 g, 4.75 mmol) and diacetoxypalladium (0.533 g, 2.37 mmol) were added, the mixture was purged with nitrogen then heated to 85°C for 3 hours. After cooling the mixture was diluted with ethylacetate (300 mL), filtered, the solid washed with ethyl acetate (2x100 mL). Filtrate was washed with water (500 mL) => _emulsion, 100 mL of brine were added to help separation of layers._ Organics were washed with brine and dried over MgSO4. Crude product (28g) was purified by flash chromatogr
The source
This record comes from experimental reaction archive (ord-03f2f90229d7474393efca5188bac2c5). Open the source and check it against what is on this page.
experimental reaction archive record ord-03f2f90229d7474393efca5188bac2c5 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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