Buchwald–Hartwig amination: 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide → Gsk-2256098
36% 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 | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Gsk-2256098 | C₂₀H₂₃ClN₆O₂ | 36.49% |
Conditions
- Temperature
- 100 °C
Yield
- 36% 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% (this run) |
| 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% |
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 sodium 2-methylpropan-2-olate (92 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) (74.1 mg, 0.13 mmol) and BIS(DIBENZYLIDENEACETONE)PALLADIUM(0) (55.3 mg, 0.10 mmol) were added and tube was sealed. Mixture was stirred at reflux overnight. Reaction was allowed to cool to room temperature, filtered, washed with CH2Cl2/MeOH (9/1, 10 mL) and concentrated to dryness. The crude product was purified by flash chromatography (dry loading) on silica gel eluting with 1 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford
The source
This record comes from experimental reaction archive (ord-9b3d4697078d49aaa1c7aef286254c96). Open the source and check it against what is on this page.
experimental reaction archive record ord-9b3d4697078d49aaa1c7aef286254c96 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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