Buchwald–Hartwig amination: 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide → Gsk-2256098
34% yield, run at 100 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide | C₁₃H₁₁Cl₂N₃O₂ | |
| Reactant | 1-Isopropyl-3-methyl-1H-pyrazol-5-amine | C₇H₁₃N₃ | |
| 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 | Gsk-2256098 | C₂₀H₂₃ClN₆O₂ | 33.86% |
Conditions
- Temperature
- 100 °C
Yield
- 34% of Gsk-2256098.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| Binap, (A+-)-; Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 47% |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | sodium 2-methylpropan-2-olate | 1,4-Dioxane | 100 °C | — | 36% |
| 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | 1,4-Dioxane | 100 °C | — | 34% (this run) |
Procedure
Copied from the source record, unedited
2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (200 mg, 0.64 mmol), 1-isopropyl-3-methyl-1H-pyrazol-5-amine (178 mg, 1.28 mmol) and cesium carbonate (313 mg, 0.96 mmol) were suspended in 1,4-dioxane (3 mL). Nitrogen was bubbled through mixture for 10 minutes. (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (27.8 mg, 0.05 mmol) and diacetoxypalladium (7.19 mg, 0.03 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight => _incomplete reaction_. Reaction was heated for a further 7 hours => _no evolution_. More Pd(OAc)2 and Xantphos were added, mixture was degassed with nitrogen and heated at reflux overnight => _complete_. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL) and concentrated to dryness. The c
The source
This record comes from experimental reaction archive (ord-0dc07c6e11344615900455301860696c). Open the source and check it against what is on this page.
experimental reaction archive record ord-0dc07c6e11344615900455301860696c 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
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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